(2-bromo-5-chloro-4-fluorophenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 227 mmol of 1-bromo-2-bromomethyl-4-chloro-5-fluoro-benzene (example 10d) in 300 ml of glacial acetic acid containing 495 mmol of potassium acetate is heated to reflux for 3 hours. The mixture is concentrated and then partitioned between water and diethyl ether. After repeated extractions with diethyl ether, the combined organic layers are washed successively with saturated sodium bicarbonate-solution solution and water, dried over magnesium sulfate and concentrated. The crude acetate is dissolved in 200 ml of methanol and treated slowly with a methanolic KOH solution (33.4 g in 100 ml). The reaction mixture is stirred for 35 minutes at room temperature, then neutralized with acetic acid and concentrated under reduced pressure. The residue is partitioned between water and diethyl ether. Concentration of the organic phase affords the crude title compound which is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value. to reflux for 3 hours The mixture is concentrated partitioned between water and diethyl ether extractions with diethyl ether the combined organic layers are washed successively with saturated sodium bicarbonate-solution solution and water dried over magnesium sulfate concentrated The crude acetate is dissolved in 200 ml of methanol treated slowly with a methanolic KOH solution (33.4 g in 100 ml) concentrated under reduced pressure The residue is partitioned between water and diethyl ether Concentration of the organic phase affords the crude title compound which is purified by flash chromatography (SiO2 60 F)