反应详情

A suspension of 5-hydroxymethyl-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran (2 g, 8.2 mmol) in toluene (20 mL) was heated until the solid dissolved. Heating was then stopped. Thionyl bromide (2.2 g, 10.6 mmol) was added, and the mixture was stirred for 1 h. Silica (25 g) was added, and the mixture was filtered, and the residue was washed with a 1:1 v/v solution of ethyl acetate and heptane. The filtrate was evaporated to give the title compound as a red-orange oil (2.6 g, 90%). 1H NMR (d6-DMSO): δ 4.72 (s, 2H), 5.11 (d, 1H), 5.28 (d, 1H), 6.17 (s, 1H), 7.04 (d, 1H), 7.17 (t, 2H), 7.33 (d, 1H), 7.38 (dd, 2H), 7.45 (s, 1H).

1. temperaturewas heated until the solid
2. dissolutiondissolved
3. temperatureHeating
4. additionSilica (25 g) was added
5. filtrationthe mixture was filtered
6. washthe residue was washed with a 1:1 v/v solution of ethyl acetate and heptane
7. customThe filtrate was evaporated