Tetrahydrofuran → HCID 17932203, compound

Participants

Reaction Steps

3-acetylphenyl carbamic acid benzyl ester (3.50 g, 13.0 mmol) was dissolved in diethyl ether (70 mL) and THF (20 mL) and brought to 0° C. A catalytic amount of aluminum (III) chloride (0.010 g) was added followed by the drop-wise addition of bromine (0.731 mL, 14.3 mmol) in diethyl ether (10 mL). The reaction was kept at 0° C. for 30 mins before being allowed to warm to room temperature on its own accord. Sat. NaHCO3 (30 mL) was added to quench the reaction and the solution was poured into ethyl acetate (30 mL). The combined organics were washed with sat. NaHCO3 (3×30 mL) and brine (1×30 mL) before being dried (Na2SO4), filtered, and evaporated to dryness. Trituration of the resulting crude product with a 2:1 mixture of dichloromethane/diethyl ether (6 mL) followed by filtration afforded 2.57 g (57%) of 3-(2-bromoacetyl)phenyl carbamic acid benzyl ester as a light pink solid: 1H NMR (400 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.11 (s, 1H), 7.69 (m, 2H), 7.43 (m, 6H), 5.18 (s, 2H), 4.88 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 201.5, 163.4, 149.8, 146.5, 144.6, 139.4, 138.5, 138.2, 133.3, 131.9, 127.6, 126.7, 76.0, 44.1; HRMS (ESI) calcd for C16H14BrNO3 (M+) 347.0157. found 347.0151.

Provenance & Evidence