tert-Butanol → [1-(4-Bromo-3-fluoro-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 1-(4-bromo-3-fluorophenyl)cyclopropanecarboxylic acid (7.4 g, 28.6 mmol, prepared from 1-bromo-4-bromomethyl-2-fluorobenzene according to Peretto et al. J Med. Chem. 2005, 48, 5705-20), DIPEA (6.36 mL, 37.1 mmol), tert-butanol (67.0 mL, 714 mmol), diphenylphosphorylazide (7.37 mL, 34.3 mmol) and molsieve (4 Å) in 100 mL toluene is stirred under reflux overnight. The reaction mixture is filtered and concentrated in vacuo. The residue is taken up in ethylacetate and washed with 5% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and brine. The organic phase is dried over MgSO4 and concentrated in vacuo. Yield: 9.37 g.

Provenance & Evidence