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

Participants

Reaction Steps

A mixture of Example 104B (5 g, 15.1 mmol), potassium carbonate (3.1 g, 22.7 mmol), and DMF (150 mL) was treated with benzyl bromide (1.8 mL, 15.1 mmol), stirred for 5 hours, and concentrated. The residue was partitioned between water (1 L) and dichloromethane (750 mL). The organic layer was washed with water and brine, dried (Na2SO4), filtered, concentrated, and purified by passing through a plug of silica gel (150 g) with 25% dichloromethane in hexane to provide the desired product. MS (ESI(−)) m/e 418, 420 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.05 (br s, 1H), 7.65 (d, 1H), 7.45 (m, 2H), 7.39 (m, 3H), 7.21 (d, 1H), 5.28 (s, 2H), 2.30 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence