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

HRID 78547노트

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HRID 78547 반응식
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]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 152610132-Bromo-5-(trifluoromethyl)benzoic acidHCID 178418244HCID 178418244, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-260dfd8883744abcb6e31cdf43accc51
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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