Dimethylformamide → N-(4-chloro-2-fluoro-3-formylphenyl)acetamide

HRID 1257161

반응식

HRID 1257161 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[CH:3]=1.C([Li])CCC.CN([CH:21]=[O:22])C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH:21]=[O:22]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 8531744'-Chloro-2'-fluoroacetanilideHCID 178418339Butyllithium

생성물 1

HCID 84784262N-(4-chloro-2-fluoro-3-formylphenyl)acetamide수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A −78° C. solution of N-(4-chloro-2-fluorophenyl)acetamide (2.00 g, 10.66 mmol) in THF (40 mL), under Ar, was treated with butyl lithium (16.66 mL, 26.7 mmol), stirred at −78° C. for 2.5 h, treated slowly with DMF (1.651 mL, 21.32 mmol), stirred for 15 min at −78° C. and slowly warmed to RT. The mixture was stirred for 2 h, treated with satd. NH4Cl, the layers separated and the aqueous layer extracted with EtOAc (1×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-chloro-2-fluoro-3-formylphenyl)acetamide (1.1 g, 48% yield) as an off-white solid. MS (ESI) m/z: 216.0 [M+H]+.

후처리

  1. stirringstirred for 15 min at −78° C.
  2. temperatureslowly warmed to RT
  3. stirringThe mixture was stirred for 2 h
  4. additiontreated with satd
  5. customNH4Cl, the layers separated
  6. extractionthe aqueous layer extracted with EtOAc (1×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. custompurified via silica gel chromatography (EtOAc/Hex)

출처 및 근거

ORD 기록
ord-78f1b2ea7d4b4c97941d6bfe608d4b03
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461179B1

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