Dimethylformamide → 2-Fluoro-4-(methoxymethoxy)-1-nitrobenzene

HRID 21512

반응식

HRID 21512 반응식
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][O:13][CH2:14]OC.CN(C)C=O.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 8020DimethoxymethaneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 5209483-Fluoro-4-nitrophenol

생성물 1

HCID 199324002-Fluoro-4-(methoxymethoxy)-1-nitrobenzene수율 31.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A solution of 3-fluoro-4-nitrophenol (10.0 g, 0.064 mol), dimethoxymethane (19.3 g, 0.255 mol) and N,N-dimethylformamide (6.0 g, 0.083 mol) in toluene is heated to 65° C., treated dropwise with phosphorus oxychloride (15.7 g, 0.102 mol), stirred at 90° C. for two hours, cooled to room temperature and poured into ice water which contains five mL of 50% sodium hydroxide solution. After the ice has melted, the mixture is extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a yellow liquid (4.0 g) which is identified by 1HNMR spectral analysis.

후처리

  1. temperaturecooled to room temperature
  2. extractionthe mixture is extracted with ether
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3714eea096134c3692e42ae9854125cb
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424280

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