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

HRID 21512

Reaction equation

HRID 21512 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3714eea096134c3692e42ae9854125cb
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Linked notes

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