Methyl 4-(bromomethyl)benzoate → HCID 69311681, compound

Participants

Reaction Conditions

Reaction Steps

Sodium t-butoxide (0.60 g, 6.34 mmol) was added all at once to a THF solution (10 mL) of 1-(3-chloro-phenyl)-propan-2-one (1.08 g, 6.40 mmol) stirred at −78° C. After 3 minutes 4-bromomethyl-benzoic acid methyl ester (1.54 g, 6.72 mmol) was added all at once and the reaction solution was allowed to warm to room temperature. After stirring for 1 hour the reaction solution was partitioned between aqueous 1N HCl and ethyl acetate. The organic phase was washed with brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.91 (d, J=8.2 Hz, 2H); 7.29-7.25 (m, 2H); 7.20 (s, 1H); 7.13 (d, J=8.2 Hz, 2H); 7.07-7.03 (m, 1H); 3.91 (broad s, 4H); 3.47 (dd, J=7.2, 13.8 Hz, 1H); 2.96 (dd, J=7.6, 13.8 Hz, 1H); 2.07 (s, 3H). LCMS1 3.66 min. (M+H)=317.

Provenance & Evidence