tert-Butyl bromoacetate → HCID 86623477, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of dry argon, a mixture of palladium dibenzylideneacetone (Pd2(dba)3, 22 mg, 0.02 mmol), di-tert-butylphosphino pentaphenylferrocene (17 mg, 0.02 mmol), 2-chloro-4-iodo-5-trifluoromethyl-pyridine (1.50 g, 4.88 mmol) and the Reformatzky reagent prepared from bromo-acetic acid tert-butyl ester and activated zinc metal (1.40 g, 5.37 mmol) is suspended in dry and degassed THF (20 ml). The mixture is heated to 60° C. After 45 minutes and after 90 minutes, additional batches of palladium dibenzylideneacetone (Pd2(dba)3, 22 mg, 0.02 mmol), di-tert-butylphosphino pentaphenylferrocene (17 mg, 0.02 mmol), and of the Reformatzky reagent (1.40 g, 5.37 mmol) are added. After a total of 2.5 h at 60° C., TLC analysis indicated complete conversion of starting materials. Upon cooling to RT, the reaction mixture is diluted with equal amounts of EtOAc and H2O, and filtered through a tight plug of cotton. The organic layer is separated, washed with brine twice, dried over Na2SO4, and the solvent is evaporated. The residue is purified by FCC (hexanes/EtOAc, gradient from 100:0 to 97:3) to afford the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.44 (s, 9H), 3.71 (s, 2H), 7.39 (s, 1H), 8.63 (s, 1H). ES+−MS: 294.1, 296.2 (Cl) [M+H]+.

Provenance & Evidence