Hydrochloric Acid → 1-(Benzyloxy)-4-bromo-2-fluorobenzene

HRID 1078023Notes

Reaction equation

HRID 1078023 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C1(=O)CCCCC1>[CH2:10]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Br:8])=[CH:7][C:2]=1[F:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneYield 97.7%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A reaction vessel was charged with 19.4 g of 2-fluoro-4-bromophenol, 12.9 g of benzyl chloride, 23.3 g of potassium carbonate and 510 ml of cyclohexanone and the reaction was carried out with stirring at 120°-140° C. for 7 hours. The reaction liquid was poured into dilute hydrochloric acid and then extracted with benzene. The benzene layer was washed with water and dried over Glauber's salt. The benzene was distilled off and the residue was purified by way of column chromatography on silica gel (eluent: hexane/benzene=4/1) to obtain 27.9 g (yield 97.3%) of 2-fluoro-4-bromophenyl benzyl ether.

Workup

  1. customThe reaction liquid
  2. extractionextracted with benzene
  3. washThe benzene layer was washed with water
  4. dry with materialdried over Glauber's salt
  5. distillationThe benzene was distilled off
  6. customthe residue was purified by way of column chromatography on silica gel (eluent: hexane/benzene=4/1)

Sources & evidence

ORD record
ord-fdf575d2ba8c498a8f550a18bcdc93be
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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