Potassium Carbonate → Tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 193 (1.90 g, 7.09 mmol), NBS (1.41 g, 7.20 mmol) and K2CO3 (1.11 g, 8.50 mmol) in MeCN (20 mL) was heated at 60° C. under N2 for 30 min. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and water. The organic layer was washed with water (×2), brine and dried. Filtration through silica gel gave tert-butyl 1-bromo-7-cyano-2-naphthylcarbamate (194) (2.45 g, 100%) as a colorless powder. A sample was recrystallised (petroleum ether) to give colorless needles: mp 139-141° C.; 1H NMR (CDCl3) δ 8.58 (d, J=9.1 Hz, 1H), 8.54 (d, J=1.0 Hz, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.56 (dd; J=8.3, 1.4 Hz, 1H), 7.36 (br s, 1H), 1.57 (s, 9H); 13C NMR δ 152.3, 136.7, 132.5, 132.0, 131.4, 129.4, 128.3, 125.6, 122.4, 119.0, 111.3, 109.4, 81.9, 28.3. Anal. (C16H15BrN2O2) C, H, N, Br.

Provenance & Evidence