Dimethylformamide → HCID 12083070, compound

Participants

Reaction Steps

1-Bromo-2-chloroethane (168 μl, 2.0 mmol) was added to 5 ml DMF in a 50 ml flask. 7-Methyl-benzo[d]isoxazol-3-ol (298 mg, 2.0 mmol), potassium carbonate (276 mg, 2.0 mmol) and additional DMF (5 ml) were added and the mixture was stirred for 12 h. Ethylacetate (50 ml) and H2O (50 ml) were added. The two phases were separated and the aqueous phase was extracted with ethylacetate. The combined organic phases were washed with brine, dried over MgSO4 and evaporated to dryness to give 420 mg of the crude product. The crude product was subjected to column chromatography (0–5% methanol in dichloromethane) to give the pure title compound 41 (290 mg, 70%). 1H NMR (CDCl3) 2.5 (s, 3H), 3.9 (t, 2H), 4.7 (t, 2H), 7.2 (t, 1H), 7.3 (d, 1H), 7.5 (d, 2H).

Provenance & Evidence