Sodium Carbonate → HCID 46312612, 화합물

HRID 1776198

반응식

HRID 1776198 반응식
Cl[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)C>[F:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=1

참가 물질

10

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 888832-Chloro-1-fluoro-3-nitrobenzeneHCID 2856454-Fluorophenylboronic acid

생성물 1

HCID 46312612HCID 46312612, 화합물수율 57.5%

시약·촉매·용매 5

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A microwave reaction vessel was charged with 2-chloro-3-fluoronitrobenzene (1.500 g, 8.5 mmol), 4-fluorophenylboronic acid (1.315 g, 9.4 mmol), sodium carbonate (2.717 g, 25.6 mmol), palladium diacetate (0.077 g, 0.3 mmol), tetrabutylammonium bromide (2.755 g, 8.5 mmol) in water (10 mL) and 1,4-dioxane (1 mL). The mixture was heated to 100° C. in a microwave reactor for 1 hr. The reaction was cooled to room temperature and poured into diethyl ether and 0.1N aqueous sodium hydroxide. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (10-30% methylene chloride/hexanes) to give the desired product as a yellow solid (1.15 g, 57%). 1H NMR (CDCl3, 300 MHz) δ 7.70 (dt, 1H, J=8.4, 1.5 Hz), 7.51 (td, 1H, J=8.4, 5.4 Hz), 7.41 (td, 1H, J=8.4, 1.2 Hz), 7.35-7.26 (m, 2H), 7.22-7.11 (m, 2H).

후처리

  1. customA microwave reaction vessel
  2. temperatureThe reaction was cooled to room temperature
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (10-30% methylene chloride/hexanes)

출처 및 근거

ORD 기록
ord-268505bdae854de2b3dbc106dcb9d4d4
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265772B2

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