Chloroacetyl chloride → N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide

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Reaction Steps

4-(tert-Butyl-dimethyl-silanyloxy)-phenylamine (2.23 g, 10 mmol) was dissolved in acetone (25 ml). After addition of Na2CO3 (3.2 g, 30 mmol), chloroacetylchloride (0.96 ml, 12 mmol) was added dropwise. After 1 hour at room temperature, the reaction mixture was quenched with H2O (100 ml) and the aqueous phase was extracted with CH2Cl2 (3×10 ml). Combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 9:1 then hexane-ethyl acetate 4:1) to provide N-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-chloro-acetamide (2.55 g, 71%) as a colorless solid, m.p. 107°-108° C. and MS: m/e=299 (M+).

Provenance & Evidence