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Hydrochloric Acid → ([1,1'-Biphenyl]-4-yl)(4-fluorophenyl)methanone

HRID 16032
Notes
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Reaction equation

HRID 16032 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.Cl>ClC1C(Cl)=C(Cl)C=CC=1>[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([C:4]2[CH:5]=[CH:6][C:1]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:2][CH:3]=2)=[O:23])=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7095BiphenylHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14549661([1,1'-Biphenyl]-4-yl)(4-fluorophenyl)methanoneYield 47%

Reagents, catalysts & solvents 1

HCID 6895
1,2,3-Trichlorobenzene
Solvent

Procedure

To a stirred solution of biphenyl (96.02 g, 0.632 mol) in trichlorobenzene (640 mL) was added aluminium chloride (91 g, 0.174 mol) in two portions. 4-Fluorobenzoyl chloride (70 mL, 0.593 mol) was then added dropwise from a dropping funnel over 1 h to the solution at 40° C., and the temperature was then raised to 100° C. for 6 h until HCl ceased to evolve. The mixture was allowed to cool to room temperature and poured into an ice/HCl mixture (ca. 2 L), and left stirring overnight. The water was decanted and the white sludge was stirred vigorously with methanol. The crude product was recovered by filtration, washed with methanol, and then dried under vacuum at 80° C. overnight This product (110 g) was recrystallised twice from toluene to give white crystals of 4-(4′-fluorobenzoyl)biphenyl (77 g, 47%); m.p. 149° C. (lit. 148.5-149° C.).

Workup

  1. waitleft
  2. customThe water was decanted
  3. stirringthe white sludge was stirred vigorously with methanol
  4. filtrationThe crude product was recovered by filtration
  5. washwashed with methanol
  6. dry with materialdried under vacuum at 80° C. overnight This product (110 g)
  7. customwas recrystallised twice from toluene

Sources & evidence

ORD record
ord-5f9cd88336b0483b803cb3d6ee742276
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07736539B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes