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

HRID 922103ノート

反応式

HRID 922103 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 576671854-Chloro-4'-fluorobiphenyl-2-amine収率 94.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a8cc7465a1084d31ab2f57396ffd0cf5
出典データセット
uspto-grants-2016_03
特許番号
US09278918B2

反応ノート

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