反应详情

To a stirred, cooled (0° C.) solution of 3′-methoxybiphenyl-3-carboxylic acid amide (0.57 g; 2.5 mmol) in dry CH2Cl2 (28 mL), under N2 atmosphere, a 1M solution of BBr3 in CH2Cl2 (6.4 mL) was added. The mixture was stirred at room temperature for 1 h, quenched with 2N Na2CO3 and extracted with AcOEt. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. Purification of residue by column chromatography (cyclohexane/EtOAc 2:8) gave the desired product as an amorphous solid. Yield 91%. Mp: 148–51° C. (after digestion with i-Pr2O). MS (EI): m/z 213 (M+, 100%). 1H NMR (CDCl3/d6-DMSO): δ 6.06 (br s, 1H); 6.59 (m, 1H); 6.85 (m, 2H); 7.01 (t, 1H); 7.23 (t, 1H); 7.35 (br s, 1H); 7.45 (m, 1H); 7.60 (m, 1H) 7.88 (s, 1H); 8.80 (s, 1H) ppm. IR (Nujol): 3314, 3141, 1669, 1630, 1607, 1577 cm−1.

1. customquenched with 2N Na2CO3
2. extractionextracted with AcOEt
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customPurification of residue by column chromatography (cyclohexane/EtOAc 2:8)