Water → 1-Bromo-2-fluoro-4-methoxybenzene

HRID 2354280Notes

Reaction equation

HRID 2354280 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[C:10](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[CH:4][C:3]=1[F:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27791534-Bromo-3-fluorophenol

Product 1

HCID 37184441-Bromo-2-fluoro-4-methoxybenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-bromo-3-fluorophenol (2.87 g) and cesium carbonate (12.2 g) in N,N-dimethylformamide (30 mL) was added methyliodide (1.87 mL) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 1-bromo-2-fluoro-4-methoxybenzene (3.02 g).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe extract was washed with water and brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1b06e58fdaff4c43a445893abbbe87c2
Source dataset
uspto-grants-2010_07
Patent number
US07750145B2

Reaction notes

Loading…