Water → Methyl 3-cyano-4-isopropoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.32 g (4.83 mmol) of methyl 3-bromo-4-isopropyloxybenzoate (from Step B), 341 mg (2.90 mmol) of zinc cyanide, 67 mg (0.12 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 44 mg (0.05 mmol) of tris(dibenzylideneacetone) dipalladium(0)-chloroform complex and 50 μL of H2O in 5.0 mL of DMF was stirred at 120° C. for 48 h. The mixture was cooled, then partitioned between EtOAc and sat'd NaCl. The aqueous layer was separated and extracted with 3× EtOAc. The organic layers were combined, dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 9:1 v/v hexanes/EtOAc gave 802 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=6.2, 6H), 3.91 (s, 3H), 4.71-4.79 (m, 1H), 6.99 (d, J=8.9, 1H), 8.18 (dd, J=2.2, 8.8, 1H), 8.24 (d, J=2.1, 1H).

Provenance & Evidence