Triethylamine → (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester

Participants

Reaction Steps

To a stirred solution of 1-fluoro-2-methoxy-4-vinylbenzene (INTERMEDIATE I.1) (4.49 g, 29.53 mmol) and 2-iodo-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester (14.89 g, 29.53 mmol) in anhydrous acetonitrile (75 mL) was added triethylamine (8.2 mL, 59.06 mmol) and tri(o-tolyl)phosphine (1.17 g, 3.84 mmol). The mixture was sparged for 5 min with argon, and palladium(II) acetate (662 mg, 2.95 mmol) was added. The mixture was heated at reflux for 13 h and concentrated to give the crude product (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester as a dark brown residue, which was used without further purification.

Provenance & Evidence