Chloroacetyl chloride → 5-fluoro-6-hydroxybenzofuran-3(2H)-one

Temperature

0 °C

A solution of 4-fluorobenzene-1,3-diol (1.00 g, 7.81 mmol) in nitrobenzene (15 mL) was added with aluminum chloride (3.12 g, 23.4 mmol), and the reaction vessel was cooled to 0° C. The reaction mixture was added dropwise with a solution of chloroacetyl chloride (1.06 g, 9.37 mmol) in nitrobenzene (2 mL), and the mixture was stirred at 40° C. for 6 hours. The reaction mixture was cooled to room temperature, and added with 2 N aqueous sodium hydroxide until the aqueous layer became basic. The aqueous layer was separated, then made acidic with 3 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 5-fluoro-6-hydroxybenzofuran-3(2H)-one (0.190 g, 14%).

1. temperatureThe reaction mixture was cooled to room temperature
2. customThe aqueous layer was separated
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated
7. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-011adc8a68a7416f82a94f1708005414

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156827B2