Cesium carbonate → 1,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 1037088노트

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HRID 1037088 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.[Cs+].[Cs+]>C1COCC1.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

6

반응물 3

HCID 10796Cesium 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 80%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of 3,4,5-trichlorophenylboronic acid (4.5 g, 20 mmol), 2-bromo-3,3,3-trifluoro-prop-1-ene (4.9 g, 28 mmol), Cs2CO3 (20 mL, 2 M, 40 mmol) and Pd(PPh3)2Cl2 (421 mg) in THF (30 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to give 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.3 g; yield 80%). 1H NMR (500 MHz, CDCl3): δ 7.40 (s, 2H), 5.99 (s, 1H), 5.76 (s, 1H) ppm.

후처리

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

출처 및 근거

ORD 기록
ord-eb6f1b55b7c34ea4840c7c6aef50e9e6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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