Carbon Dioxide → 2-(4-Cyano-3-(trifluoromethyl)phenyl)acetic acid

HRID 82212노트

반응식

HRID 82212 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1.[C:22](=[O:24])=[O:23].[Cl-].[NH4+].Cl>C1COCC1.CCOC(C)=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH2:9][C:22]([OH:24])=[O:23])=[CH:11][C:12]=1[C:18]([F:19])([F:20])[F:21])#[N:15]

참가 물질

8

반응물 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27755974-Methyl-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 708173812-(4-Cyano-3-(trifluoromethyl)phenyl)acetic acid수율 88%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

Lithium diisopropylamide (13.8 mL, 24.8 mmol, 1.8M in THF) was added to 4-methyl-2-(trifluoromethyl)benzonitrile (2.30 g, 12.4 mmol) in THF (20 mL) at −78° C. and stirred for minutes at −78° C. Excess solid carbon dioxide was added then the mixture was stirred at room temperature for 17 hours. Saturated aqueous ammonium chloride (10.5 mL) and EtOAc (20 mL) were added then the aqueous layer was acidified with HCl acid solution (1 M). This was extracted with EtOAc (3×15 mL) and the combined organic phases were dried over sodium sulphate and evaporated in vacuo to afford the title compound as a brown oil in 88% yield, 2.52 g.

후처리

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. extractionThis was extracted with EtOAc (3×15 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulphate
  4. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-50b433557be24735b22fb818da78e671
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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