Water → 2-Chloro-3-(trifluoromethyl)benzaldehyde

HRID 1096833노트

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HRID 1096833 반응식
[Li]CCCC.[F:6][C:7]([F:16])([F:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].CN([CH:20]=[O:21])C.O>C1COCC1>[Cl:14][C:9]1[C:8]([C:7]([F:6])([F:15])[F:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:20]=[O:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 69211-Chloro-2-(trifluoromethyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 27366722-Chloro-3-(trifluoromethyl)benzaldehyde수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-70 °C

실험 절차

BuLi (1.6 M in hexane, 173 mL, 277 mmol) was added to a sol. of 2-trifluoromethyl-chlorobenzene (50.0 g, 277 mmol) in THF (500 mL) at −70° C. The sol. was stirred for 2 h at −70° C., and DMF (21.3 mL, 277 mmol) in THF (100 mL) was added. The mixture was allowed to warm to rt overnight. Water was added (200 mL), and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 20:1) yielded the title compound (37.4 g, 65%). LC-MS: tR=0.96 min.

후처리

  1. temperatureto warm to rt overnight
  2. extractionthe mixture was extracted with Et2O (2×)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (heptane/EtOAc 20:1)

출처 및 근거

ORD 기록
ord-43cb4c74db514d84b642b57af4708b1f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138340B2

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