Triethylamine → 5-Bromo-2-(trifluoromethoxy)benzonitrile

HRID 1747508노트

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HRID 1747508 반응식
C([N:3]([CH2:6][CH3:7])CC)C.CCCP(=O)=O.[Br:14][C:15]1[CH:16]=C[C:18]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([CH:22]=1)C=O.Cl.ON.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:14][C:15]1[CH:22]=[CH:19][C:18]([O:23][C:24]([F:25])([F:26])[F:27])=[C:7]([CH:16]=1)[C:6]#[N:3]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 16167369Propylphosphoric anhydrideHCID 265992015-Bromo-2-(trifluoromethoxy)benzaldehyde

생성물 1

HCID 451081625-Bromo-2-(trifluoromethoxy)benzonitrile수율 86.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Triethylamine (1.14 mL, 8.18 mmol) and propylphosphonic anhydride (cyclic trimer) (ca. 1.7 M solution in ethyl acetate, 4.8 mL, 8.18 mmol) were added in this order to a solution of 5-bromo-2-(trifluoromethoxy)benzaldehyde (2.00 g, 7.43 mmol) and hydroxyamine hydrochloride (568 mg, 8.18 mmol) in DMF (7.5 mL), and the mixture was stirred at 100° C. for 8 hours. The reaction solution was poured to a saturated sodium bicarbonate aqueous solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2] to obtain the title compound (1.71 g, yield: 86%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate=100/0-98/2]

출처 및 근거

ORD 기록
ord-fbffe86c42274eaba2b208d8911af331
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150575B2

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