Sodium Fluoride → 3beta-Acetoxy-5alpha,6beta-dichloro-14alpha-fluoropregnan-20-one

3β-Acetoxy-5α,6β-dichloropregnan-20-one (1.4 g) was dissolved in fluorotrichloromethane (250 ml) and chloroform (200 ml) containing sodium trifluoroacetate (ca. 2 g) and sodium fluoride (ca. 2 g). The resulting solution was cooled to -78° and vigourously stirred, whereupon fluorine from four 750 cc bottles (10% v/v fluorine in nitrogen) was bubbled through the solution over a period of 8 hours. The reaction solution was then poured into aqueous sodium thiosulphate and the organic layer was separated, washed with water, dried over potassium carbonate and evaporated to dryness to yield crude 3β-acetoxy-5α,6β-dichloro-14α-fluoropregnan-20-one.

1. temperatureThe resulting solution was cooled to -78°
2. customwas bubbled through the solution over a period of 8 hours
3. additionThe reaction solution was then poured into aqueous sodium thiosulphate
4. customthe organic layer was separated
5. washwashed with water
6. dry with materialdried over potassium carbonate
7. customevaporated to dryness

ORD record

ord-234168b7e3f6491997a2f83d137b1c78

Source dataset

uspto-grants-1981_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04284558