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With dihydrogen peroxide; sodium hydroxide; for 3h;
To a 250 mL round bottom flask, ZBC 103 (3 g) and 2N NaOH (40 mL) were added and the reaction vessel was cooled to 0 C. Then 30% hydrogen peroxide (4 mL) was slowly added. The reaction mixture was stirred at 0 C for 3 h. Subsequently, the reaction mixture was acidified with 2N HC1 at 0 C to afford the solid compound. The solid material was collected by filtration and dried to obtain the title compound. ESI-MS calculated for C7H6BrC1NO2 [M+Hj = 249.9; Observed: 250.11.
(6-amino-2-bromo-3-chlorophenyl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
120 mg
To a 250 niL round bottom flask, ZBC 104 (170 mg) and THF (40 mL) were added and the reaction vessel was cooled to 0 C. Then LiAlH4 (60 mg) was slowly added. The reaction mixture was stirred at 0 C for 3 h. Then 2 N NaOH (15 mL) was added. After 30 min, the solvent was evaporated under vacuum. The remaining residues was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The remaining residues were purified by flash column chromatography on silica gel to afford ZBC 105-1 in 120 mg. ESI-MS calculated for C7H8BrClNO [M+H]+ = 235.94; Observed: 236.05. 1H NMR (400 MHz, CDC13) delta 7.21 (d, = 8.6 Hz, 1H), 6.62 (d, = 8.6 Hz, 1H), 4.97 (s, 2H).
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