5-Fluoro-2-nitrophenol → HCID 19702686, compound

HRID 406044Notes

Reaction equation

HRID 406044 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH:12]1(O)[CH2:16][CH2:15][CH:14]=[CH:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)Cl>[CH:16]1([O:8][C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:9]([O-:11])=[O:10])[CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

6

Reactant 3

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 2201642-Cyclopentene-1-ol

Product 1

HCID 19702686HCID 19702686, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-fluoro-2-nitrophenol (1.48 g), 2-cyclopenten-1-ol (662 mg) and triphenylphosphine (2.47 g) in THF (25.0 ml) diethylazodicarboxylate (1.48 ml) was added at 0° C. After stirring at room temperature overnight the reaction mixture was diluted with methylene chloride and washed with 10% aq. KHSO4. The organic layer was passed through a hydrophobic frit and concentrated in vacuo. The residue was purified by chromatography to give the desired product.

Workup

  1. additionwas added at 0° C
  2. washwashed with 10% aq. KHSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-f3bc10177a25481598859b4ea9f16987
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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