Carbon tetrabromide → Ethyl 2-[4-(bromomethyl)phenoxy]acetate

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Reaction Steps

To a 1 L round bottomed flask with a stirring bar, addition funnel and an argon inlet was added ethyl 2-(4-hydroxymethylphenoxy)acetate 35-4 (7.47 g, 35.53 mmol), CBr4 (13.26 g, 39.97 mmol) and dry CH2Cl2 (300 mL). This solution was cooled in an ice bath and and a solution of triphenyl phosphine (10.48 g, 39.97 mmol) in CH2Cl2 (100 mL) was added dropwise over 1 h. The ice bath was allowed to expire and and the mixture was stirred at ambient temperature 18 h. The solvent was removed in vacuo and the residue was chromatographed directly on 200 g of silica gel useing 15% EtOAc-hexane as eluant. There was obtained ethyl 2-(4-bromomethylphenoxy)acetate 35-5 (7.2 g, 74%) as a low melting solid, mp.: 44°-45° C. 1H NMR (CDCl3): δ 1.29 (t, J=7 Hz, 3H), 4.26 (q, J=7 Hz, 2H), 4.48 (s, 2H), 4.61 (s, 2H), 6.86 (d, J=9 Hz, 2H), 7.32 (d, J=9HZ, 2H).

Provenance & Evidence