Water → HCID 20498427, compound

Temperature

20 °C

The contents of a 10 ml flask charged with 1,1,1-tribromo-3-methyl-2-butanol (1.7 mmol), mesyl chloride (1.9 mmol) and pyridine (6 ml) were stirred at 20° C. for 16 hours. Then, the reaction mixture was poured out into water (50 ml), then extracted with three 15 ml-portions of dichloromethane, the combined extract phases were washed with 15 ml 36% (w) aqueous hydrochloric acid, dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried liquid to leave a residue (0.9 g) of methyl 1,1,1-tribromo-3-methyl-2-butyl sulphonate (compound 13). The contents of a 10-ml flask charged with this sulphonate (0.50 mmol), zinc powder (0.75 mmol), diethyl ether (2.5 ml) and glacial acetic acid (0.5 ml) were stirred at 20° C. for 30 min. The sulphonate was fully converted, with a selectivity to the title compound of 82%.

1. extractionextracted with three 15 ml-portions of dichloromethane
2. extractionthe combined extract phases
3. washwere washed with 15 ml 36% (w) aqueous hydrochloric acid
4. dry with materialdried over anhydrous magnesium sulphate
5. customthe solvent was evaporated from the dried liquid

ORD record

ord-0ddd7610043444388e473557196c92c4

Source dataset

uspto-grants-1981_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04307243