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Water → 2-[(3,5-Difluoro-2-nitrophenoxy)methyl]oxirane

HRID 496215
Notes
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Reaction equation

HRID 496215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Br.O>CN(C=O)C.C(OCC)(=O)C>[F:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH:3]=[C:2]([F:1])[CH:7]=1)[O:12][CH2:19][CH:21]1[CH2:22][O:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 118195353,5-Difluoro-2-nitrophenol

Product 1

HCID 223137492-[(3,5-Difluoro-2-nitrophenoxy)methyl]oxiraneYield 121.9%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3,5-difluoro-6-nitrophenol (100 mg, 0.571 mmol) and potassium carbonate (394 mg) in DMF (5 ml) was added epibromohydrin (80 mg, 0.582 mmol) and was stirred at 70° C. for 3 hr. Water and ethyl acetate were added, the organic phase separated, dried and concentrated. The resulting residue was purified by chromatography (ethyl acetate:heptan 1:3) to give the desired product as a solid 161 mg (0.696 mmol).

Workup

  1. customthe organic phase separated
  2. customdried
  3. concentrationconcentrated
  4. customThe resulting residue was purified by chromatography (ethyl acetate:heptan 1:3)

Sources & evidence

ORD record
ord-a748725c68934af1baae83ec59e6dc32
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06943188B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes