N-bromobutanimide → 2-Bromo-1-[6-(difluoromethoxy)pyridin-3-yl]ethan-1-one

HRID 633769ノート

反応式

HRID 633769 の反応式
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]([F:17])[F:16])=[N:12][CH:13]=1)=[CH2:7])CCC.[Br:18]N1C(=O)CCC1=O>C1COCC1.O.O>[Br:18][CH2:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 118199865HCID 118199865、化合物

生成物 1

HCID 1181998662-Bromo-1-[6-(difluoromethoxy)pyridin-3-yl]ethan-1-one収率 75.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

A solution of 100 mg (0.41 mmol) of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine in 4 mL of THF/H2O (3/1: v/v) is cooled to 0° C. 74 mg (0.41 mmol) of N-bromosuccinimide are then added in a single portion. The yellow solution is stirred at 0° C. for 1 hour and then taken up in water and extracted with EtOAc. The organic phase is washed with saturated aqueous NaHCO3 solution and then with saturated NaCl solution, dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes) to give 82 mg of 2-bromo-1-(6-difluoromethoxypyrid-3-yl)ethanone, corresponding to the following characteristics:

後処理

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  3. dry with materialwith saturated NaCl solution, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes)

出典と根拠

ORDレコード
ord-f36da45fcf604d4fb0169556ec4d7c5b
出典データセット
uspto-grants-2016_04
特許番号
US09321790B2

反応ノート

読み込み中…