Sodium hydride → HCID 67376843, compound

Participants

Reaction Steps

To a stirred slurry of NaH (60% in mineral oil) (0.435 mL, 10.00 mmol) in THF (5 ml) was added dropwise a solution of 2-bromo-3-methylaniline (0.625 mL, 5 mmol) in THF (1 ml). After 15 min, (2-bromoethoxy)-tert-butyldimethylsilane (1.07 mL, 5 mmol) was added and the reaction mixture was stirred for 48 h. The reaction was quenched with water, partitioned between EtOAc and aqueous saturated ammonium chloride. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (0-10% EtOAc/hexanes). 2-Bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline was isolated as a yellow oil.

Provenance & Evidence