Benzyl Bromide → Benzyl 3-bromo-6-[(tert-butoxycarbonyl)amino]-2-methylbenzoate

Participants

Reaction Steps

A mixture of Example 104B (10 g, 30.3 mmol), potassium carbonate (6.3 g, 45.4 mmol), and DMF (300 mL) was treated with benzyl bromide (3.6 mL, 30.3 mmol), stirred for 5 hours, concentrated, and partitioned between water (1 L) and ethyl acetate (1 L). The organic layer was washed with water (2×1 L) and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI(+)) m/e 420, 422 (M+H)+, 437, 439 (M+NH4)+, 442, 444 (M+Na)+; (ESI(−)) m/e 418, 420 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.04 (s, 1H), 7.65 (d, 1H), 7.45 (m, 2H), 7.37 (m, 3H), 7.22 (d, 1H), 5.28 (s, 2H), 2.30 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence