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

HRID 2309305노트

반응식

HRID 2309305 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
114 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8be4a4a319654d538d6dc7b1d475ba0b
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04695131

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