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

HRID 532151노트

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HRID 532151 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c16bde3d71104befa489ca074c9ea321
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853186B2

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