Methanol → HCID 53739261, compound

Participants

Reaction Steps

A mixture of 7-bromo-2-methyl-benzo[b]thiophene (Acheson, R. M.; Cooper, M. W. J. Chem. Soc., Perkin Trans 11980, 1185), (0.88 g, 3.89 mmol), with Pd(OAc)2 (176.4 mg), dppf (637.2 mg), Et3N (3.0 mL) and CH3OH (17 mL) in DMSO (26 mL) is reacted at 80° C./1100 psi of CO for 24 h. The crude reaction mixture is diluted with EtOAc (100 mL), washed with 0.1 M HCl (3×30 mL); dried with Na2SO4; filtered and concentrated. Purification of the crude material by silica gel chromatography to give the title compound (0.66 g, 3.19 mmol, 82%). 1H NMR (CDCl3): δ 2.63 (s, 3H), 4.02 (s, 3H), 7.04 (q, J=0.9 Hz, 1H), 7.38 (t, J=7.9 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 8.01 (dd, J=8.0, 1.3 Hz, 1H) ppm. ES-MS (m/z): calcd for C11H10O2S (M+NH4)+: 224.3. found: 224.1.

Provenance & Evidence