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

HRID 1913614

반응식

HRID 1913614 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

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”).

후처리

  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

출처 및 근거

ORD 기록
ord-7b255a3e9862460898aaa4fb157998b5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609705B2

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