Toluene → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

HRID 51964

반응식

HRID 51964 반응식
C1(C)C=CC=CC=1.[F:8][C:9]([F:26])([F:25])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22](O)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1.S(Cl)([Cl:29])=O>CN(C=O)C>[F:8][C:9]([F:26])([F:25])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:22]([Cl:29])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acid2회

생성물 1

HCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chloride

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a nitrogen purged 3 liter 4-neck flask fitted with a condenser, mechanical stirrer, temperature probe, and connected to a 2M aqueous NaOH scrubber was added toluene (1 L), 4′-trifluoromethyl-biphenyl-2-carboxylic acid (250 g, 0.94 mol, 1 equiv), and DMF (5 mL). 4′-Trifluoromethyl-biphenyl-2-carboxylic acid can be obtained from Aldrich, Milwaukee, Wis. The solution was heated to 60° C. and thionyl chloride (110 mL, 1.5 mol, 1.6 equiv) was added at such a rate as to maintain the temperature below 65° C. The addition was complete after 30 minutes and the reaction was heated to reflux. After 4 hours, the heating was stopped and the reaction was allowed to stir overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was used in the next step without further purification. The material crystallized to a solid at room temperature.

후처리

  1. customTo a nitrogen purged 3 liter 4-neck flask
  2. customfitted with a condenser, mechanical stirrer
  3. temperatureto maintain the temperature below 65° C
  4. additionThe addition
  5. temperaturethe reaction was heated to reflux
  6. waitAfter 4 hours
  7. concentrationThe reaction mixture was concentrated in vacuo
  8. customthe residue was used in the next step without further purification
  9. customThe material crystallized to a solid at room temperature

출처 및 근거

ORD 기록
ord-b541533d9a334318badf7770b41c8ee0
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713489B2

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