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

HRID 82212ノート

反応式

HRID 82212 の反応式
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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50b433557be24735b22fb818da78e671
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

反応ノート

読み込み中…