HCID 22144837, compound → 1-(2-Bromo-4-fluoro-phenoxy)-2-methyl-propan-2-ol
Reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6](=[O:8])[CH3:7].[CH3:14][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([CH3:14])([OH:8])[CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Cool a solution of 1-(2-bromo-4-fluoro-phenoxy)-propan-2-one (520 mg, 2.10 mmol) in THF (4 mL) to 0° C. in an ice bath under nitrogen. Add methylmagnesium chloride (3.0 M in THF, 0.84 mL, 2.53 mmol) dropwise. Stir the mixture at 0° C. for an additional half an hour. Add water and extract with ethyl acetate. Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (hexane to 30% ethyl acetate in hexane) to give the title compound as a yellow oil (230 mg, 42%). MS (ES) m/z 285 [M+Na]+.