Sodium Chloride → 1-(Benzyloxy)-2-bromo-4-fluorobenzene

HRID 2219461Notes

Reaction equation

HRID 2219461 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CN(C)C=O>[CH2:16]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 216409031-(Benzyloxy)-2-bromo-4-fluorobenzeneYield 91%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2-bromo-4-fluorophenol (24.7 g, 129 mmol), tetrabutylammonium iodide (4.8 g, 13.0 mmol), potassium carbonate (35.9 g, 260 mmol) and N,N-dimethylformamide (390 mL), benzyl bromide (23.5 g, 137 mmol) was added at room temperature and stirred for 1.5 hours. The reaction mixture was poured into a mixture of ethyl acetate and saturated aqueous sodium chloride, and then extracted with ethyl acetate. The organic phase was washed twice with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20) to give 1-benzyloxy-2-bromo-4-fluoro-benzene (33.0 g, 90%).

Workup

  1. additionwas added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed twice with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10-80:20)

Sources & evidence

ORD record
ord-a57c18d0a7374137a05320d751558bc8
Source dataset
uspto-grants-2008_08
Patent number
US07414072B2

Reaction notes

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