Benzyl chloroformate → benzyl N-(5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate

Participants

Reaction Steps

To a solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (23.57 mmol, 5 g) in ethyl acetate (40 mL) was added potassium carbonate (47.1 mmol, 6.52 g) as a solution in water (40.0 mL). The whole was stirred vigorously before benzyl chloroformate (25.9 mmol, 3.65 mL, 4.42 g) was added and stirring continued overnight. The reaction was quenched with more water and was extracted with DCM (2×). The organic layers were separated and dried using a hydrophobic frit, and were concentrated in vacuo to give desired product as a brown solid (5.5 g, 15.9 mmol, 67.4%). 1H NMR (400 MHz, CDCl3) δ 1.82 (m, 1H) 2.60 (m, 1H) 2.85 (m, 1H) 2.90 (m, 1H), 4.95 (d, 1H) 5.18 (m, 3H) 7.18 (d, 1H) 7.34 (m, 7H).

Provenance & Evidence