1-Bromo-3-chlorobenzene → (R)-tert-butyl 2-(3-chlorobenzoyl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3-chlorobenzene (5 g, 18.2 mmol) in anhydrous THF (25 mL) at −78° C. under nitrogen was added dropwise a solution of 2.5 M n-BuLi in hexane (18.2 mmol). After stirring for 1 h at −78° C., a solution of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (3.47 g, 18.2 mmol) in anhydrous THF (10 mL) was added dropwise. After addition, the reaction mixture was allowed to warm to rt and stirred for 2 h. Tlc indicated the reaction was complete. The mixture was quenched with satd aq NH4Cl (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the crude product (5.5 g, 93%), which was used immediately for next step without purification.

Provenance & Evidence