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Thionyl chloride (5.9 mL) was added to 2 g (8 mmol) of 2-iodobenzoic acid under stirring
and was refluxed for 1 h. After cooling the reaction mixture, excess thionyl chloride
was removed in vacuo to give the 2-iodobenzoyl chloride which was used without further
purification. To a solution of the above 2-iodobenzoyl chloride in CH2Cl2, 2 equiv of benzyl amine (1.76 mL) were added and the mixture was stirred at r.t.
for 2 h. The reaction mixture was washed with EtOAc and the solvent was removed in
vacuo. The crude product was purified by dry column chromatography affording the desired
N-benzyl-2-iodobenzamide (2.4 g, yield 88%). 1H NMR (300 MHz, CDCl3, 25 °C): d = 7.85 (d, 1 H, J = 9 Hz), 7.25-7.42 (m, 7 H), 7.05-7.11 (m, 1 H), 6.05 (s, 1 H), 4.64 (d, 2 H, J = 6 Hz). To a solution of N-benzyl-2-iodobenzamide (2.4 g, 7.1 mol) in CH2Cl2 (50 mL), oxone (5.7 g, 1.3 equiv) was added. The reaction mixture was warmed to 40-45
°C over 20 min and stirred at this temperature for 24 h (0.21 g, yield 20%). 1H NMR (300 MHz, DMSO-d
6, 25 °C): d = 9.89 (t, 1 H, J = 6 Hz), 8.30 (d, 1 H, J = 6 Hz), 8.22 (d, 1 H, J = 6 Hz), 7.95 (t, 1 H, J = 15 Hz), 7.75 (t, 1 H, J = 15 Hz), 7.27-7.36 (m, 5 H), 4.58 (d, 2 H, J = 6 Hz).
<A NAME="RU24604ST-15">15</A>
2,6-Dichlorophenol (22 mg, 0.135 mmol) was added to a solution of IBX amide (100 mg,
0.27 mmol) and TEAB (57 mg, 0.27 mmol) in DMSO (2 mL). After 0.5 h, the reaction mixture
was diluted with H2O (20 mL), extracted with Et2O (6 × 20 mL), and the organic layers was dried (MgSO4) and evaporated. The crude product was purified by dry column chromatography to give
4-bromo-2,6-dichlorophenol (30.6 mg, yield 94%).
