Isopropenyl acetate → HCID 20134188, compound

Participants

Reaction Steps

Tributyltin methoxide (80.3 mL, 279 mmol), methyl 3-bromobenzoate (53.5 g, 249 mmol), isopropenyl acetate (39.4 ml, 358 mmol), palladium(II) acetate (2.6 g, 11.6 mmol) and tri-ortho-tolylphosphine (7.1 g, 23.2 mmol) were stirred together in toluene (350 mL) at 100° C. under nitrogen for 18 hours. After cooling, the reaction was treated with potassium fluoride solution (4M, 560 ml) and stirred for 2 hours. The resulting mixture was diluted with further toluene (200 mL) and filtered through Celite®, washing the filter pad with ethyl acetate. The organic phase was separated, dried (sodium sulfate) and reduced in vacuo. The residue was purified by chromatography eluting with ethylacetate:pentane 10:90 to 20:80 to give the title compound (45.3 g) as an orange oil. 1H NMR (400 MHz, CDCl3) δ: 2.18 (3H, s), 3.75 (2H, s), 3.91 (3H, s), 7.43-7.37 (2H, m), 7.87 (1H, s), 7.95-7.93 (1H, d); LRMS ESI m/z 215 [M+Na]+, 191 [M−H]−.

Provenance & Evidence