Chloroform → 3-bromo-4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridine N-oxide

HRID 2094365

反応式

HRID 2094365 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.C(Cl)(Cl)Cl.ClC1C=CC=C(C(OO)=[O:33])C=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N+:4]([O-:33])[CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][C:11]=2[N:12]=1

参加物

5

反応物 3

HCID 6212ChloroformHCID 70297m-Chloroperbenzoic acidHCID 668809172-(3-Bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole

生成物 1

HCID 668801883-bromo-4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridine N-oxide収率 70.7%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 0.50 g of 2-(3-bromopyridin-4-yl)-5-(trifluoromethyl)benzoxazole and 5 ml of chloroform, 0.58 g of 65% m-chloroperbenzoic acid was added. The reaction mixture was stirred while heating at 50° C. for 1.5 hours. The reaction mixture was cooled to room temperature, then diluted with ethyl acetate, and washed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and a saturated sodium chloride solution, sequentially. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.37 g of 3-bromo-4-[5-(trifluoromethyl)benzoxazole-2-yl]pyridine N-oxide (hereinafter, referred to as “active compound 28”).

後処理

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate (twice) and a saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-432f4b1e30a046169c006169f3637b2f
出典データセット
uspto-grants-2013_05
特許番号
US08445522B2

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