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

HRID 532155ノート

反応式

HRID 532155 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-03943589c3a249c4a59da2da6ddc3d61
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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