Dimethylformamide → 4-(Trifluoromethyl)pyridine-2-carbaldehyde

HRID 2071089ノート

反応式

HRID 2071089 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[Li]CCCC.CN([CH:20]=[O:21])C>CCOCC>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH:20]=[O:21])[CH:7]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 147614714-(Trifluoromethyl)pyridine-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To 2-bromo-4-(trifluoromethyl)pyridine (700 mg, 3.1 mmol) in ether (30 ml) at −78° C., BuLi (1.6M in hexanes, 2.13 ml) was added. After 40 min, DMF (340 mg) was added and the reaction mixture was stirred at −78° C. for a further 45 minutes and the reaction mixture was allowed to come to rt over a period of 1 h. Then the reaction mixture was quenched with solid ammonium chloride and partitioned between water and ether. Organic layers were dried and evaporated to provide 4-(trifluoromethyl)picolinaldehyde as a crude residue which was carried to the next step without further purification.

後処理

  1. waitto come to rt over a period of 1 h
  2. customThen the reaction mixture was quenched with solid ammonium chloride
  3. custompartitioned between water and ether
  4. customOrganic layers were dried
  5. customevaporated

出典と根拠

ORDレコード
ord-7e1bf1bd0fb64035859c6490de490d03
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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