Hydrochloric Acid → 2-Fluoro-4-bromo-4'-acetylbiphenyl

HRID 2396660Notes

Reaction equation

[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([F:22])[CH:11]=1.Cl>C(Cl)Cl>[C:5]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=2[F:22])=[CH:21][CH:20]=1)(=[O:7])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A reaction vessel was charged with 113 g of anhydrous aluminum chloride and 600 ml of methylene chloride. To the mixture was added dropwise 113 g of acetyl chloride with stirring at a temperature not higher than 0° C., and was then added dropwise a solution of 100 g of 4-bromo-2-fluoro-biphenyl in 400 ml of methylene chloride. The mixture was reacted with stirring for 7 hours while gradually bringing it back to room temperature. The reaction liquid was poured into ice and diluted hydrochloric acid. The methylene chloride layer was washed successively with water, an aqueous solution of sodium hydrogen carbonate and water, and then dried over Glauber's salt. The solvent was then distilled off and the residue was recrystallized from acetone to give 96 g (82.2%) of 4-acetyl-2'-fluoro-4'-bromobiphenyl.

Workup

customThe mixture was reacted
stirringwith stirring for 7 hours
customback to room temperature
customThe reaction liquid
washThe methylene chloride layer was washed successively with water
dry with materialan aqueous solution of sodium hydrogen carbonate and water, and then dried over Glauber's salt
distillationThe solvent was then distilled off
customthe residue was recrystallized from acetone

Sources & evidence

ORD record: ord-034e2127cc6145bc8806fa6d1580a81c
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05494605

Reaction notes

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