Dimethylformamide → 2-Formyl-5-(trifluoromethyl)benzoic acid

HRID 78547ノート

反応式

HRID 78547 の反応式
C([Li])CCC.CCCCCC.Br[C:13]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].CN(C)[CH:28]=[O:29].[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCCC1>[CH:28]([C:13]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=[O:29]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 152610132-Bromo-5-(trifluoromethyl)benzoic acidHCID 178418244HCID 178418244、化合物

生成物 1

HCID 866408592-Formyl-5-(trifluoromethyl)benzoic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a 250 mL round-bottomed flask, was added 2.5 M n-butyllithium/hexane (8.92 mL, 22.30 mmol) in tetrahydrofuran (40 mL) and cooled to −78° C., followed by dropwise addition of 2-bromo-5-(trifluoromethyl)benzoic acid (3 g, 11.15 mmol) in tetrahydrofuran (20 mL). After 30 min N,N-dimethylformamide (0.978 g, 13.38 mmol) was added and the solution slowly allowed to warm to rt. To the reaction was added saturated ammonium chloride solution, followed by addition of saturated NaHCO3 solution until basic. The aqueous layer was separated, and 2 N HCl was added until acidic. The mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried, filtered, and concentrated. The resulting solid was used without further purification. MS (DCI/NH3) m/z 512 (M+NH4)+.

後処理

  1. temperatureto warm to rt
  2. customThe aqueous layer was separated
  3. addition2 N HCl was added until acidic
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was used without further purification

出典と根拠

ORDレコード
ord-260dfd8883744abcb6e31cdf43accc51
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

反応ノート

読み込み中…