Cesium carbonate → 4-Chloro-4'-fluorobiphenyl-2-amine

HRID 922103노트

반응식

HRID 922103 반응식
Br[C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[Cl:9][C:6]1[CH:5]=[C:3]([NH2:4])[C:2]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 113102762-Bromo-5-chloroaniline

생성물 1

HCID 576671854-Chloro-4'-fluorobiphenyl-2-amine수율 94.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

2-Bromo-5-chloroaniline (CAS#823-57-4; 5 g), 4-fluorophenylboronic acid (3.56 g) and cesium carbonate (31.6 g) were combined in THF (70 ml) and water (35 ml). The mixture was degassed by bubbling argon through the solution. After addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture was stirred 1 h at 80° C. in a sealed tube. The reaction mixture was diluted with EtOAc, washed with water, dried over Na2SO4, evaporated and purified by chromatography (silica gel, 0% to 30% EtOAc in heptane). The product was finally bulb-to-bulb distilled at 0.3 mbar and 120-130° C. oven temperature to give the title compound (5.07 g) as a light yellow liquid.

후처리

  1. customThe mixture was degassed
  2. customby bubbling argon through the solution
  3. additionAfter addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture
  4. additionThe reaction mixture was diluted with EtOAc
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. custompurified by chromatography (silica gel, 0% to 30% EtOAc in heptane)
  9. distillationdistilled at 0.3 mbar and 120-130° C. oven temperature

출처 및 근거

ORD 기록
ord-a8cc7465a1084d31ab2f57396ffd0cf5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278918B2

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