2,4-Difluoroaniline → HCID 11312546、化合物

HRID 896078ノート

反応式

HRID 896078 の反応式
FC1C=C(F)C=CC=1N.CC([O-])(C)C.[Na+].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:24])=[CH:19][CH:18]=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[OH:24])=[CH:21][CH:22]=1

参加物

6

反応物 3

HCID 97092,4-DifluoroanilineHCID 112086704-BROMO-2'-CHLOROBENZOPHENONEHCID 23676156Sodium t-butoxide

生成物 1

HCID 11312546HCID 11312546、化合物収率 51.7%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

2,4-Difluoroaniline (0.28 ml; 2.7 mmol), NaOtBu (260 mg; 2.7 mmol), Pd(OAc)2 (10 mg; 0.04 mmol), R-(+)-BINAP (10 mg; 0.02 mmol) and (4-bromo-phenyl)-(2-chloro-phenyl)-methanone (200 mg; 0.67 mmol) are dissolved in dioxan (3 ml) and refluxed for 20 min. The reaction mixture is poured on water and extracted with TBME twice. The combined organic phases are dried over Na2SO4, evaporated to dryness and purified via chromatography (SiO2; TBME/hexanes 5/95>2/8) to yield the title compound (103 mg; 44%) as brownish crystals. Recrystallisation from acetone hexanes yields colorless crystals (48 mg; 21%).

後処理

  1. temperaturerefluxed for 20 min
  2. additionThe reaction mixture is poured on water
  3. extractionextracted with TBME twice
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated to dryness
  6. custompurified via chromatography (SiO2; TBME/hexanes 5/95>2/8)

出典と根拠

ORDレコード
ord-b1e56401ea334921aa144689718b6042
出典データセット
uspto-grants-2005_07
特許番号
US06919336B2

反応ノート

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