Fluorobenzene → 4-Fluoro-4'-(phenylethynyl)benzophenone

HRID 2241064Notes

Reaction equation

HRID 2241064 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Br[C:25]1C=CC(C(Cl)=O)=C[CH:26]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([C:25]#[C:26][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 10008FluorobenzeneHCID 685154-Bromobenzoyl chlorideHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

Procedure

4-bromo-4′-fluorobenzophenone: fluorobenzene (6.89 g, 71.7 mmol), 4-bromobenzoyl chloride (7.86 g, 35.8 mmol), and aluminum chloride (4.78 g, 35.8 mmol) were combined and stirred for 24 h at room temperature. The resulting mixture was poured over ice, and then filtered. The solid was dissolved in hot ethanol, treated with decolorizing charcoal, and filtered; white crystals of the title compound formed upon cooling of the ethanol solution and were isolated by filtration.

Workup

  1. additionThe resulting mixture was poured over ice
  2. filtrationfiltered
  3. dissolutionThe solid was dissolved in hot ethanol
  4. additiontreated with decolorizing charcoal
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0527158bd23b437c89564e249cb30f69
Source dataset
uspto-grants-2010_05
Patent number
US07723458B2

Reaction notes

Loading…