Benzyl Bromide → HCID 58913477, compound

HRID 1296942Notes

Reaction equation

HRID 1296942 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([F:9])=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.[Cl-].[Na+].O>[CH2:17]([O:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([Cl:8])=[CH:7][C:2]=1[Br:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 189975962-Bromo-4-chloro-5-fluoro-phenol

Product 1

HCID 58913477HCID 58913477, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Bromo-4-chloro-5-fluoro-phenol (1 eq) was taken up in DMF. Caesium Carbonate (2.5 eq) was added and the solution was stirred for 5 minutes. Benzyl bromide (1.05 eq) was added and all was stirred at room temperature for 3 hours under nitrogen. The reaction mixture was diluted with brine and extracted into diethyl ether. The organic phase was washed several time with brine, dried over MgSO4, filtered and concentrated in vacuo, to give 1-benzyloxy-2-bromo-4-chloro-5-fluoro-benzene as an oil, which solidified on standing.

Workup

  1. stirringall was stirred at room temperature for 3 hours under nitrogen
  2. extractionextracted into diethyl ether
  3. washThe organic phase was washed several time with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fd5969c8f574f7b9d2d59ce8b10cddc
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

Loading…