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

HRID 532155노트

반응식

HRID 532155 반응식
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].Br[C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].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:9][C:6]1[CH:5]=[C:4]([C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21])[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 532171832-(3,5-Dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 584682331,3-Dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene수율 56.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A mixture of 2-(3,5-dichloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.56 g, 8.83 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (1.85 g, 10.6 mmol), Cs2CO3 (11.5 mL, 2M, 17.7 mmol) and Pd(PPh3)2Cl2 (200 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 on silica gel eluted with hexanes to give 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1.3 g; yield 56%) as colorless oil. 1H NMR (500 MHz, CDCl3): δ 7.412 (d, J=6.5 Hz, 2 H), 6.057 (s, 1 H), 5.806 (s, 1 H) 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 on silica gel
  7. washeluted with hexanes

출처 및 근거

ORD 기록
ord-03943589c3a249c4a59da2da6ddc3d61
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853186B2

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