Acetonitrile → Benzyl 5-fluoro-3-methoxy-2-nitrophenyl ether

HRID 2305624Notes

Reaction equation

HRID 2305624 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C.O>[CH2:23]([O:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([O:12][CH3:13])[CH:3]=[C:2]([F:1])[CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 184333835-Fluoro-3-methoxy-2-nitrophenol

Product 1

HCID 18433397Benzyl 5-fluoro-3-methoxy-2-nitrophenyl etherYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-fluoro-3-methoxy-2-nitrophenol(0.56 g), acetonitrile(5 mL), potassium carbonate(0.46 g) and benzyl bromide(0.56 g) was stirred at reflux for 2 h. The cooled mixture was treated with water and ethyl acetate and the organic phase was separated, washed with brine, dried and evaporated to dryness. The residue was purified by flash chromatography eluting with increasingly polar mixtures of ethyl acetate and hexane to give the product (0.82 g), (m/e278, MH+).

Workup

  1. temperatureat reflux for 2 h
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography
  7. washeluting
  8. temperaturewith increasingly polar mixtures of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9f390cfb9c314121956502886bc17132
Source dataset
uspto-grants-2002_08
Patent number
US06441012B1

Reaction notes

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