Acetic Acid → HCID 66849502, compound

Participants

Reaction Steps

To a solution of methyl 2-amino-5-bromobenzoate (10.0 g, 43.5 mmol) in dichloromethane (0.5 M, 90 mL) at 0° C. were added p-anisaldehyde (7.9 mL, 65 mmol) and acetic acid (1.2 mL, 22 mmol). Sodium triacetoxyborohydride (18.4 g, 87.0 mmol) was added portion-wise to the solution mixture. The reaction was allowed to warm to room temp and stirred overnight. Upon completion, the reaction was poured into saturated sodium bicarbonate (200 mL). The product was extracted with dichloromethane (3×75 mL). The combined organic extractions were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified via flash chromatography (silica, 1:1 hexanes/dichloromethane) to yield methyl 5-bromo-2-[(4-methoxybenzyl)amino]benzoate. HRMS (M+H)=350.0381. 1H NMR (400 MHz, CDCl3) 8.08 (b, 1H), 8.10 (d, 1H), 7.36 (dd, 1H), 7.24 (d, 2H), 6.88 (d, 2H), 6.54 (d, 1H), 4.35 (s, 2H), 3.86 (s, 3H), 3.80 (s, 3H).

Provenance & Evidence