Potassium Carbonate → 1,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 532151ノート

反応式

HRID 532151 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].Br[C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([C:16]([F:19])([F:18])[F:17])=[CH2:15])[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 248204653,4,5-Trichlorophenylboronic acid

生成物 1

HCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene収率 90%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 3,4,5-trichlorophenylboronic acid (3.376 g, 15 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (4.02 g, 23 mmol), K2CO3 (4.15 g, 30 mmol) and Pd(PPh3)2Cl2 (4.15 g, 30 mmol) in THF (16 mL) and H2O (8 mL) was heated at 80° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between EA (50 mL) and H2O (50 mL). The aqueous layer was extracted with EA (50 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel to give the crude desired product (3.7 g; 90% yield) as a pale yellow solid.

後処理

  1. temperatureThe mixture was cooled to rt
  2. custompartitioned between EA (50 mL) and H2O (50 mL)
  3. extractionThe aqueous layer was extracted with EA (50 mL)
  4. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-c16bde3d71104befa489ca074c9ea321
出典データセット
uspto-grants-2014_10
特許番号
US08853186B2

反応ノート

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