2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,1':4',1''-Terphenyl, 2'-fluoro-4''-propyl-

HRID 2309305Notes

Reaction equation

HRID 2309305 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([F:22])[CH:11]=2)=[CH:6][CH2:5]1)[CH2:2][CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:22][C:12]1[CH:11]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=2)[CH:15]=[CH:14][C:13]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 201841732-Fluoro-4-(4-propyl-1-cyclohexen-1-yl)-1,1′-biphenyl

Product 1

HCID 17156651,1':4',1''-Terphenyl, 2'-fluoro-4''-propyl-Yield 101.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
114 °C

Procedure

A solution of 4-(4-n-propylcyclohexenyl)-2-fluorobiphenyl (20 gram) in toluene (120 ml) was added over a 25 minute period with stirring to a suspension of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (34 gram) in toluene (200 ml). The temperature rose from 19° C. to 24° C. over the addition, after which time the reaction mixture was heated under reflux (114° C.) for 3 hours. The reaction mixture was cooled, filtered, the filtrate and toluene washings (100 ml) were combined and then washed with saturated sodium metabisulphite solution (250 ml). The organic extract was further washed with water (2×250 ml), dried and evaporated to dryness to give a brown residue (20.1 gram). The residue was dissolved in dichloromethane (120 mls) and adsorbed onto a column of basic alumina (60 gram) over silica gel (60 gram). Elution with dichloromethane (450 ml) gave on evaporation of the solvent an off white solid (14 gram) which was recrystallised from ethanol (80 mls) to yield a white crystalline product (12.8 gram) m.p. 75°-77° C.

Workup

  1. additionThe temperature rose from 19° C. to 24° C. over the addition
  2. temperatureafter which time the reaction mixture was heated
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washwashed with saturated sodium metabisulphite solution (250 ml)
  6. extractionThe organic extract
  7. washwas further washed with water (2×250 ml)
  8. customdried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-8be4a4a319654d538d6dc7b1d475ba0b
Source dataset
uspto-grants-1987_09
Patent number
US04695131

Reaction notes

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