2-(Trimethylsilyl)ethanol → Trimethylsilanylethyl 2-fluoro-4-iodobenzoate

Participants

Reaction Steps

To a solution of 115.5 mg (0.4 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 10 mL of dichloromethane (under a blanket of argon) was added 91.5 mg (0.5 mmol) of 1-(3-dimethylaminopropyl-3-ethyl carbodiimide hydrochloride) and 53 mg (0.4 mmol) of 4-dimethylaminopyridine. To this reaction mixture was added 0.16 ml (132 mg, 1.1 mmol) of 2-trimethylsilylethanol and the resultant mixture was allowed to stir at ambient temperature for 23 hours. The reaction mixture was extracted between ethyl ether and water and the layers were separated. The aqueous phase was washed with ethyl ether (2×50 mL) and the organic phases were combined. The combined organic phase was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to a clear, colorless oil. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) gave the title compound as a clear, colorless oil. PMR (CDCl3): δ 0.07 (9 H, s), 1.13 (2 H, dd, J=8.5, 10.3 Hz), 4.42 (2 H, q, J=8.5, 10.3 Hz), 7.50-7.70 (3 H, m).

Provenance & Evidence