Nitromethane → (E)-Benzyl 2-fluoro-3-(2-nitrovinyl)phenylcarbamate

HRID 2361328노트

반응식

HRID 2361328 반응식
[F:1][C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:21]([CH3:24])([O-:23])=[O:22]>C(O)(=O)C>[F:1][C:2]1[C:7](/[CH:8]=[CH:24]/[N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 6375Nitromethane2회HCID 86681522Benzyl 2-fluoro-3-formylphenylcarbamate

생성물 1

HCID 70651607(E)-Benzyl 2-fluoro-3-(2-nitrovinyl)phenylcarbamate수율 68.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of benzyl 2-fluoro-3-formylphenylcarbamate (4.0253 g, 14.73 mmol), nitromethane (1.98 mL, 36.8 mmol) and nitromethane (1.979 mL, 36.8 mmol) in acetic acid (49.1 mL) under nitrogen was heated at 90° C. After 2 hr, the reaction was cooled to room temperature and concentrated in vacuo. The residue was dissolved in CH2Cl2 (75 mL) and water (75 mL), and Na2CO3 (s) was added until pH basic by litmus paper. After separation of layers, the aqueous layer was extracted with CH2Cl2 (3×75 mL). The organic layers were combined and washed with brine (50 mL), dried over MgSO4, and concentrated in vacuo to give the desired product (4.251 g, 10.08 mmol, 68.4% yield) as a burgundy oil.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (75 mL)
  3. additionwater (75 mL), and Na2CO3 (s) was added until pH basic by litmus paper
  4. customAfter separation of layers
  5. extractionthe aqueous layer was extracted with CH2Cl2 (3×75 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9bd2afb22c0e404b94ad67c5ef414342
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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