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

HRID 61913
Notes
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Reaction equation

HRID 61913 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-79c7e601161647efaa727e13ebaddad9
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440922B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes