Ammonium Chloride → 2-(2-Bromo-4-methoxyphenyl)propan-2-ol

HRID 2275291

Reaction equation

HRID 2275291 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[CH3:13][Mg+].[Br-].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([OH:12])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 106570061-(2-Bromo-4-methoxyphenyl)ethan-1-oneHCID 178418689HCID 178418689, compound

Product 1

HCID 668348332-(2-Bromo-4-methoxyphenyl)propan-2-olYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of 1-(2-bromo-4-methoxyphenyl)-ethanone (300 mg) dissolved in THF solution (3 ml), MeMgBr (3 M THF solution, 0.52 ml) was added at 0° C. under nitrogen atmosphere. Then, the mixture was stirred at room temperature for 6 hrs. The reaction mixture was added with saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with saturated brine, and the residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (220 mg, 69%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-93e71be7dfd04c3ba162528591e90903
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Linked notes

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