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

HRID 1753086ノート

反応式

HRID 1753086 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 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).

後処理

  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

出典と根拠

ORDレコード
ord-463c15d2143c44799a32bb1ad0b2fd86
出典データセット
uspto-grants-2015_10
特許番号
US09163021B2

反応ノート

読み込み中…