Hydrochloric Acid → HCID 66893680, compound

Temperature

-78 °C

To a solution of 1-(2-fluoro-3-hydroxy-phenyl)-ethanone (8.50 g, 55.0 mmol) in tetrahydrofuran (80 mL) was slowly added a methyl magnesium bromide solution in diethyl ether (3.0 M, 46.5 mL, 0.15 mol) at −78° C. The resulting mixture was stirred at −78° C. for 10 min and then allowed to come to room temperature and stirred for an additional 40 min. The reaction mixture was diluted with diethyl ether (100 mL) and cooled in an ice bath before an aqueous hydrochloric acid solution (1N, 200 mL) was added dropwise. The biphasic mixture was separated and the aqueous phase extracted with diethyl ether (2×60 mL). The combined organic phases were washed with water, brine and dried over sodium sulfate. The resulting mixture was filtered and evaporated and the resulting oil was dried under vacuum which afforded 2-fluoro-3-(1-hydroxy-1-methyl-ethyl)-phenol (9.40 g, 100%) as an off-white solid.

1. customto come to room temperature
2. stirringstirred for an additional 40 min
3. additionwas added dropwise
4. customThe biphasic mixture was separated
5. extractionthe aqueous phase extracted with diethyl ether (2×60 mL)
6. washThe combined organic phases were washed with water, brine
7. dry with materialdried over sodium sulfate
8. filtrationThe resulting mixture was filtered
9. customevaporated
10. customthe resulting oil was dried under vacuum which

ORD record

ord-4563da37b353401782af473e097776a1

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741327B2