Toluene → HCID 57552550, compound

Participants

Reaction Conditions

Reaction Steps

Charge an oven-dried 250 mL round-bottom flask with 6-methoxy-1-tetralone (3.0 g, 17.0 mmol.) and place under nitrogen. Dissolve the solid in toluene (30 mL) and add 1-bromo-3-fluorobenzene (4.7 mL, 42.6 mmol), sodium t-butoxide (6.5 g, 68.1 mmol), palladium acetate (76 mg, 0.34 mmol), and racemic BINAP (212 mg, 0.34 mmol). Heat the solution to 115° C. and stir for 18 hours. Dilute the solution with cold 5N HCl (50 mL) and ethyl acetate (200 mL). Separate the organic layer and dry over sodium sulfate, filter over a pad of celite and concentrate in vacuo. Purify the crude product using radial chromatography to give 3.4 g (74%) of the title compound. This material is used without further purification: mass spectrum (ion spray) m/z=267 (M−H).

Provenance & Evidence