2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2,3-Difluorobiphenyl

HRID 327372Notes

Reaction equation

HRID 327372 reaction equation
C([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])=[CH:8][CH2:7]1)CCCC.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:19][C:13]1[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 144956434-Pentyl-(2,3-difluorophenyl)-cyclohexene

Product 1

HCID 130223872,3-Difluorobiphenyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 0.1 mol 4-pentyl-1-(2,3-difluorphenyl)-cyclohex-1-en and 500 ml toluene is added 0.22 mol 2,3-dichlor-5,6-dicyano-p-benzoquinone (DDQ) and refluxed for 2 h. After usual work-up 2',3'-difluorbiphenyl, bp: 125° C. at 0.5 mm Hg is obtained.

Workup

  1. temperaturerefluxed for 2 h

Sources & evidence

ORD record
ord-fb1dae48ed244936ae7d49afde158323
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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