Hydrochloric Acid → 4-Bromo-2-fluoro-1-(hexyloxy)benzene

HRID 1078024Notes

Reaction equation

HRID 1078024 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].Cl>C1(=O)CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 194309624-Bromo-2-fluoro-1-(hexyloxy)benzeneYield 83.7%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A reaction vessel was charged with 19.4 g of 2-fluoro-4-bromophenol, 16.8 g of hexyl bromide, 23.3 g of potassium carbonate and 510 ml of cyclohexanone and the reaction was effected with stirring at 120°-140° C. for 7 hours. The reaction liquid was poured into dilute hydrochloric acid and the mixture was extracted with benzene. The benzene layer was washed with water and dried over Glauber's salt, and the benzene was distilled off. The residue was purified by way of column chromatography on silica gel (eluent: hexane) to obtain 23.4 g (yield 83.6%) of 3-fluoro-4-hexyloxybromobenzene.

Workup

  1. customThe reaction liquid
  2. extractionthe mixture was extracted 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)

Sources & evidence

ORD record
ord-ee97a81e4a1e4928827badfd5eba8e83
Source dataset
uspto-grants-1996_08
Patent number
US05545747

Reaction notes

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