Cesium carbonate → 6-Chloro-4'-fluorobiphenyl-3-ol

HRID 1619705노트

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HRID 1619705 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1I.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:11][C:12]1[C:17]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 229287294-Chloro-3-iodophenol

생성물 1

HCID 580423356-Chloro-4'-fluorobiphenyl-3-ol수율 70.3%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
75 °C

실험 절차

A solution of 4-fluorophenylboronic acid (500 mg, 3.57 mmol), 4-chloro-3-iodophenol (455 mg, 1.79 mmol) and caesium carbonate (1.75 g) in dioxane (10 mL) and water (5 mL) was degassed 1 hour with nitrogen. Tetrakis(triphenylphosphine)palladium (0) (104 mg, 0.09 mmol) was added and the reaction mixture was heated for 18 hours at 75° C. The cooled reaction mixture was concentrated in vacuo and the residual aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layer were dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20% ethyl acetate in heptane to afford the title compound (280 mg, 70%) as a yellow oil.

후처리

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. extractionthe residual aqueous layer was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layer were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 20% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-d8fa635e944240298921f269f1f5ebe6
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772293B2

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