4-(5-Fluoro-2-methoxyphenyl)-4-methylpentan-2-one → 1-Bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one

HRID 458126Notes

Reaction equation

HRID 458126 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([C:8]([CH3:14])([CH3:13])[CH2:9][C:10](=[O:12])[CH3:11])[CH:7]=1.[Br-:17].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl.CO>[Br:17][CH2:11][C:10](=[O:12])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:15][CH3:16])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 222849224-(5-Fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 222849461-Bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of the above ketone (1.34 g, 6 mmol) in methylene chloride (35 mL) and MeOH (5 mL), benzyltrimethylammonium tribromide (2.57 g, 6.6 mmol) was added at ambient temperature. After 30 minutes, TLC (hexanes-EtOAc (9:1)) showed complete disappearance of the starting material. The reaction mixture was diluted with methylene chloride (50 mL), washed with two 50 mL portions of water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 1-bromo-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one as a light brown liquid (80%) which was used for the next reaction without further purification.

Workup

  1. washwashed with two 50 mL portions of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26894b8d00704cf2a3b79cb0a2abedce
Source dataset
uspto-grants-2007_03
Patent number
US07189758B2

Reaction notes

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