Dichloromethane → 2-(3-Methoxy-4-nitrophenyl)acetonitrile

HRID 1262316

반응식

HRID 1262316 반응식
C(OC(=O)[CH:7]([C:19]#[N:20])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=1)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O>>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([CH2:7][C:19]#[N:20])[CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66712431Tert-butyl 2-cyano-2-(3-methoxy-4-nitrophenyl)acetate

생성물 1

HCID 136293172-(3-Methoxy-4-nitrophenyl)acetonitrile수율 61.8%

실험 절차

Into a 1-neck round-bottom flask, Cyano-(3-methoxy-4-nitro-phenyl)-acetic acid tert-butyl ester (12.80 g, 43.79 mmol), Methylene chloride (50 g, 600 mmol), and Trifluoroacetic Acid (20 mL, 200 mmol) were added and stirred at room temperature overnight. The solvent was removed under vacuum. The residual TFA was co-evaporated with DCM three times to give brown oil. The reaction was partitioned with saturated NaHCO3 and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant. The collected fractions afforded as a light brown solid. The solid was triturated with Et2O to give (3-Methoxy-4-nitro-phenyl)-acetonitrile as a light yellow solid (5.20 g, 61%).

후처리

  1. customThe solvent was removed under vacuum
  2. customto give brown oil
  3. customThe reaction was partitioned with saturated NaHCO3 and DCM
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum
  10. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant
  11. customThe collected fractions afforded as a light brown solid
  12. customThe solid was triturated with Et2O

출처 및 근거

ORD 기록
ord-69ce3fe35b6d451a85948b9f7bde68dd
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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