Hydrochloric Acid → HCID 19379480, compound

HRID 1769567Notes

Reaction equation

HRID 1769567 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[F:15])=[CH:4][CH:3]=1.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].Cl>CC(=O)CC>[CH2:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=2[F:15])=[CH:6][CH:7]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81731-BromodecaneHCID 11430Potassium CarbonateHCID 14204869HCID 14204869, compound

Product 1

HCID 19379480HCID 19379480, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A reaction vessel was charged with 12 g of 4-hydroxy-2'-fluoro-4'-bromobiphenyl obtained in Example 4(b), 14.2 g of decyl bromide, 15.7 g of potassium carbonate and 100 ml of 2-butanone (MEK), and the mixture was refluxed with stirring for 12 hours (the disappearance of the starting materials were confirmed by TLC). The reaction liquid was poured into diluted hydrochloric acid and the mixture was extracted with benzene. The extract was washed with water and dried over Glauber's salt. The solvents were distilled off and the residue was purified by way of column chromatography on silica gel (eluent:hexane) and then recrystallized from hexane to obtain 14.9 g (81.5%) of 4-decyloxy-2'-fluoro-4'-bromobiphenyl.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe reaction liquid
  3. extractionthe mixture was extracted with benzene
  4. washThe extract was washed with water
  5. dry with materialdried over Glauber's salt
  6. distillationThe solvents were distilled off
  7. customthe residue was purified by way of column chromatography on silica gel (eluent:hexane)
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-bab3b35384f14f91ab815ef9c61cab52
Source dataset
uspto-grants-1995_01
Patent number
US05382380

Reaction notes

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