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

HRID 21512

反応式

HRID 21512 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

HCID 199324002-Fluoro-4-(methoxymethoxy)-1-nitrobenzene収率 31.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3714eea096134c3692e42ae9854125cb
出典データセット
uspto-grants-1995_06
特許番号
US05424280

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