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

HRID 1753086노트

반응식

HRID 1753086 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 5 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) was added and the aqueous layer was acidified with 1M HCl. The mixture 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 (88%, 2.52 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. extractionThe mixture 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-463c15d2143c44799a32bb1ad0b2fd86
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163021B2

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