Acetic Acid → HCID 68614959, compound

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.

1. temperatureto reflux for 3 hours
2. concentrationThe mixture is concentrated
3. custompartitioned between water and diethyl ether
4. extractionextractions with diethyl ether
5. washthe combined organic layers are washed successively with saturated sodium bicarbonate-solution solution and water
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. dissolutionThe crude acetate is dissolved in 200 ml of methanol
9. additiontreated slowly with a methanolic KOH solution (33.4 g in 100 ml)
10. concentrationconcentrated under reduced pressure
11. customThe residue is partitioned between water and diethyl ether
12. customConcentration of the organic phase affords the crude title compound which
13. customis purified by flash chromatography (SiO2 60 F)

ORD record

ord-03fd5eefc7324a2281d0fda1ddf5b442

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324235B2