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

HRID 1492352Notes

Reaction equation

HRID 1492352 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneYield 60.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g of 4-bromo-2-fluorophenol, 19 g of potassium carbonate and 100 ml of acetone was refluxed under stirring for 30 minutes. The reaction mixture was cooled, to which 17.40 g of benzyl chloride were dropwise added taking 15 minutes. The resultant was refluxed under stirring for 7 hours and filtered. The filtrate was distilled to remove acetone. The residue to which water was added was extracted with chloroform. The extract was washed, dried and purified by a silica gel column chromatography using chloroform. The eluate was evaporated under reduced pressure to obtain 22.24 g of the intended benzyl 4-bromo-2-fluorophenyl ether.

Workup

  1. temperaturewas refluxed
  2. additionwere dropwise added
  3. waittaking 15 minutes
  4. temperatureThe resultant was refluxed
  5. stirringunder stirring for 7 hours
  6. filtrationfiltered
  7. distillationThe filtrate was distilled
  8. customto remove acetone
  9. additionThe residue to which water was added
  10. extractionwas extracted with chloroform
  11. washThe extract was washed
  12. customdried
  13. custompurified by a silica gel column chromatography
  14. customThe eluate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d45ce3d3e01c403e9146a014aae0f696
Source dataset
uspto-grants-1994_12
Patent number
US05374373

Reaction notes

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