Methanol → Methyl 2-(chloromethyl)-4-phenoxybenzoate

Participants

Reaction Steps

To a solid mixture of 5-phenoxy-3H-isobenzofuran-1-one (65.54 g, 0.29 mol), boric acid (538 mg, 8.7 mmol) and triphenylphosphine oxide (2.42 g, 8.7 mmol) was added thionyl chloride (42.3 mL). The resulting mixture was refluxed overnight. After cooled, methanol (300 mL) was slowly added to the reaction mixture. It was then refluxed for 1 h and concentrated. Residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to provide the title compound (87.02 g, 0.31 mol) as an oil. It was used directly to the next reaction without further purification. 1H NMR in CDCl3, δ in ppm: 7.91 (d, 1H, 8.6 Hz), 7.5-6.9 (m, 7H), 5.06 (s, 2H), 3.83 (s, 3H).

Provenance & Evidence