HCID 22144837, compound → 1-(2-Bromo-4-fluorophenoxy)-2-methyl-2-propanol

HRID 558138Notes

Reaction equation

HRID 558138 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

HCID 22144837HCID 22144837, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 574450921-(2-Bromo-4-fluorophenoxy)-2-methyl-2-propanolYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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]+.

Workup

  1. extractionAdd water and extract with ethyl acetate
  2. washWash the solution with aqueous saturated sodium chloride
  3. dry with materialDry over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (hexane to 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-39201a298dce482ca6825ab9709ef4a9
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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