Triethylamine → HCID 57458159, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-6-tert-butylnaphthalene (980 mg, 3.72 mmol), palladium acetate (84 mg, 0.37 mmol), 1,3-bis(diphenylphosphino)propane (153 mg, 0.37 mmol) and triethylamine (1.56 ml, 11.2 mmol) in methanol (6 ml) and DMF (10 ml) was heated at 80° C. under carbon monoxide gas pressure (balloon) for 15 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate-toluene (8:1)(160 ml) and filtered through a pad of celite. The filtrate and washings were washed with water, brine, dried over sodium sulfate and evaporated in vacuo to give the crude product which was purified through silica gel column chromatography, eluting with hexane/EtOAc (10:1), to furnish the title compound as colorless oil (843 mg, 94%). 1H NMR (300 MHz, CDCl3): δ 1.43 (9H, s), 3.97 (3H, s), 7.61-7.67 (1H, m), 7.79-7.93 (3H, m), 8.01-8.07 (1H, m), 8.57 (1H, br, s).

Provenance & Evidence