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

HRID 51964

反応式

HRID 51964 の反応式
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

参加物

5

反応物 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acid2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b541533d9a334318badf7770b41c8ee0
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

関連ノート

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