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1 Supporting Information Bromination of Deactivated Aromatic Compounds with Sodium Bromide/Sodium Periodate under Mild Acidic Conditions Lalit Kumar,* Tanu Mahajan and D. D. Agarwal Department of Industrial Chemistry, Jiwaji University, Gwalior , Madhya Pradesh, India. Phone: Contents 1. Reagents and analytics S2 2. Analytical data of compounds 1, 2, 3, 4, 5, 6, 7, 8 and 9 S2-S4 3. Spectra of compounds 1, 2, 3, 4, 5, 6, 7, 8 and 9 1 (GC/MS, 1 H-NMR, 13 C-NMR and IR) S4-S7 2 (MS and IR)..S7-S8 3 (MS and IR)..S8-S9 4 ( 1 H-NMR and 13 C-NMR).S9-S10 5 (MS, IR, 1 H-NMR and 13 C-NMR)...S10-S12 6 ( 1 H-NMR and 13 C-NMR).S12-S13 7 (GC/MS, IR, 1 H-NMR and 13 C-NMR).S14-S17 8 (MS, IR and 1 H-NMR).S18-S19 9 (MS, IR and 1 H-NMR).S19-S20 S1
2 1. Reagents and Analytics. Sodium bromide (NaBr), sodium periodate (NaIO 4 ) and all of the aromatic substrates were obtained from commercial suppliers and were used without further purification. Doubly distilled water was used all through the study. GC/MS analyses were carried out using Agilent GC (Model 5893) with Chemstation software; column-hp5-ms, 30 m x 0.25 mm x 0.25 micron; detector- mass; mass range- 14 amu to 650 amu; flow- 2 ml/min (constant flow); injector temp- 270 o C; detector temp- 300 o C; injection volume- 1 microliter of 5 % solution in methanol. 1 H and 13 C-NMR spectra were obtained in DMSO-d 6 and CDCl 3 solutions on a Bruker Avance II 400 NMR spectrometer; the chemical shifts were reported in δ ppm, relative to tetramethylsilane (TMS) as an internal standard. Mass spectra were recorded on Micromass Quattro Micro API triple quadrupole MS equipped with a standard APCI ion source. IR spectra were recorded on a Shimadzu Prestize 21 FT-IR Spectrometer. The melting points were determined by using Buchi apparatus and the yields were calculated by weight. The structures of the products were confirmed by comparison of their spectral data and physical constants with those of the authentic samples. 2. Analytical data of compounds 1, 2, 3, 4, 5, 6, 7, 8 and 9 3-Bromobenzoic acid (1): White crystalline powder; Recrystallization from petroleum ether; mp o C (lit o C). 1 H NMR (400 MHz, DMSO): δ (s, 1H, COOH), 8.06 (t, 1H, Ar), 7.92 (dt, 1H, Ar), 7.75 (dt, 1H, Ar), 7.43 (t, 1H, Ar). 13 C NMR (100 MHz, DMSO): , , , , , 128, IR (KBr): 3089, 2606, 1686, 1559, 1438, 1273, 836, 751, 706, 671, 650 cm -1. MS m/z calculated for C 7 H 5 BrO , found Bromonitrobenzene (2): Light yellow crystals; Recrystallization from petroleum ether; mp 50 o C (lit o C). 1 H NMR (400 MHz, CDCl 3 ): δ 7.45 (t, 1H, J = 8.2 Hz), 7.84 (d, 1H, J = 8.2 Hz), 8.19 (d, 1H, J = 8.2 Hz), 8.40 (s, 1H). IR (KBr): 3089, 2867, 1660, 1600, 1577, 1530, 1270, 852, 800, 728, 663, 650 cm -1. MS m/z calculated for C 6 H 4 BrNO 2 202, found Bromo-4-chlorobenzene (3): White crystalline powder; Recrystallization from ethanol; mp o C (lit o C). 1 H NMR (200 MHz, CDCl 3 ): δ 7.07 (d, 2H, J = 8.54 Hz), 7.28 (d, 2H, J = 8.54 Hz). S2
3 IR (KBr): 3084, 2955, 1887, 1626, 1499, 1389, 1254, 811, 770, 724, 496, 479 cm -1. MS m/z calculated for C 6 H 4 BrCl 191.5, found Bromo-3,5-dinitrobenzene (4): Yellow solid; Recrystallization from hexane; mp o C (lit. 77 o C). 1 H NMR (300 MHz, CDCl 3 ): δ 8.7 (s, 2H), 9.01 (s, 1H). 13 C NMR (75 MHz, CDCl 3 ): 117.7, 123.9, 132.1, IR (KBr): 3095, 2873, 1808, 1614, 1594, 1346, 1307, 1160, 1072, 1000, 914, 894, 836, 725, 636, 514, 487 cm -1. MS m/z calculated for C 6 H 3 BrN 2 O 4 247, found Bromo-2-nitrobenzaldehyde (5): Off-white solid; Recrystallization from hexane; mp 95 o C (lit o C). 1 H NMR (300 MHz, CDCl 3 ): δ 7.84 (d, 1H, J = 8.29 Hz), 7.90 (m, 1H, J = 1.4, 1.7, 4.9 Hz), 8.27 (d, 1H, J = 1.7 Hz), (s, 1H). 13 C NMR (75 MHz, CDCl 3 ): 127.6, 130.9, 137.2, IR (KBr): 3093, 1798, 1690, 1592, 1557, 1529, 1347, 1270, 1096, 1073, 889, 820, 722, 658, 511 cm - 1. MS m/z calculated for C 7 H 4 BrNO 3 230, found Bromo-5-nitrobenzaldehyde (6): Off-white crystalline solid; Recrystallization from hexane; mp o C (lit. 100 o C). 1 H NMR (300 MHz, CDCl 3 ): δ 8.36 (s, 1H), 8.63 (s, 1H), 8.66 (s, 1H), (s, 1H). 13 C NMR (75 MHz, CDCl 3 ): 123.0, 124.1, 131.6, 137.5, 138.4, 149.2, MS m/z calculated for C 7 H 4 BrNO 3 229, found Bromo-2-chlorobenzoic acid (7): White crystalline needles; Recrystallization from ethyl acetate; mp o C (lit o C). 1 H NMR (400 MHz, DMSO): δ (s, 1H, COOH), 7.94 (d, 1H, Ar), 7.57 (dd, 1H, Ar), 7.38 (d, 1H, Ar). 13 C NMR (100 MHz, DMSO): , , , , , , IR (KBr): 3094, 2989, 1703, 1678, 1581, 1465, 1271, 1053, 831, 818, 733, 662, 514 cm -1. MS m/z calculated for C 7 H 4 BrClO , found 236. Bromobenzene (8): Colorless liquid; bp o C (lit o C). 1 H NMR (200 MHz, CDCl 3 ): δ 7.5 (d, 2H, J = 8.0 Hz), 7.2 (d, 3H, J = 8.0 Hz). IR (KBr): 3066, 1573, 1476, 1443, 1069, 1020, 988, 735, 684, 672 cm -1. MS m/z calculated for C 6 H 5 Br 157, found Bromonaphthalene (9): Yellowish-red liquid; bp 280 o C (lit o C). 1 H NMR (200 MHz, CDCl 3 ): δ 8.21 (d, 1H, J = 8.0 Hz), (d, 3H, J = 6.0 Hz), (m, 2H), (t, 1H, S3
4 J = 8.0 Hz). IR (KBr): 3055, 1591, 1562, 1502, 1377, 1252, 1200, 1161, 1135, 1022, 957, 790, 764, 652 cm -1. MS m/z calculated for C 10 H 7 Br 207.1, found 206. Figure S1: GC/MS of 3-bromobenzoic acid (1) S4
5 Figure S2: 1 H-NMR spectra of 3-bromobenzoic acid (1) S5
6 Figure S3: 13 C-NMR spectra of 3-bromobenzoic acid (1) S6
7 Figure S4: IR spectra of 3-bromobenzoic acid (1) Figure S5: MS spectra of 3-bromonitrobenzene (2) S7
8 Figure S6: IR spectra of 3-bromonitrobenzene (2) Figure S7: MS spectra of 1-bromo-4-chlorobenzene (3) S8
9 Figure S8: IR spectra of 1-bromo-4-chlorobenzene (3) Figure S9: 1 H-NMR spectra of 1-bromo-3,5-dinitrobenzene (4) S9
10 Figure S10: 13 C-NMR spectra of 1-bromo-3,5-dinitrobenzene (4) Figure S11: MS spectra of 4-bromo-2-nitrobenzaldehyde (5) S10
11 Figure S12: IR spectra of 4-bromo-2-nitrobenzaldehyde (5) Figure S13: 1 H-NMR spectra of 4-bromo-2-nitrobenzaldehyde (5) S11
12 Figure S14: 13 C-NMR spectra of 4-bromo-2-nitrobenzaldehyde (5) Figure S15: 1 H-NMR spectra of 3-bromo-5-nitrobenzaldehyde (6) S12
13 Figure S16: 13 C-NMR spectra of 3-bromo-5-nitrobenzaldehyde (6) S13
14 Figure S17: GC/MS spectra of 5-bromo-2-chlorobenzoic acid (7) S14
15 Figure S18: IR spectra of 5-bromo-2-chlorobenzoic acid (7) S15
16 Figure S19: 1 H-NMR spectra of 5-bromo-2-chlorobenzoic acid (7) S16
17 Figure S20: 13 C-NMR spectra of 5-bromo-2-chlorobenzoic acid (7) S17
18 Figure S21: MS spectra of bromobenzene (8) Figure S22: IR spectra of bromobenzene (8) S18
19 Figure S23: 1 H-NMR spectra of bromobenzene (8) Figure S24: MS spectra of 1-bromonaphthalene (9) S19
20 Figure S25: IR spectra of 1-bromonaphthalene (9) Figure S26: 1 H-NMR spectra of 1-bromonaphthalene (9) S20
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