4-Chloro-2-nitrophenol → HCID 22064360, compound

HRID 1827868Notes

Reaction equation

HRID 1827868 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].[CH:12]1(O)[CH2:16][CH:15]=[CH:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH:15]2[CH2:14][CH:13]=[CH:12][CH2:16]2)=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1

Participants

5

Reactant 3

HCID 69804-Chloro-2-nitrophenolHCID 11776TriphenylphosphineHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 22064360HCID 22064360, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-nitro-4-chlorophenol (3.46 g, 20 mmol), 3-cyclopenten-1-ol (2.1 g, 24 mmol), triphenylphosphine on polystyrene (3.0 mmol per gram, 10 g, 30 mmol) and di-tert-butyl azadicarboxylate (6.9 g, 30 mmol) in THF (200 mL ) was shaken for 1 hour and filtered. The resin was washed with dichloromethane (4×50 mL). The combined organic solutions were mixed with 20 g of silica gel and then concentrated to dryness. The residue was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes to provide 4.08 g (85%) of the desired product. 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=2.4 Hz, 1H), 7.46 (dd, J=8.8, 2.7 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 5.75 (br s, 2H), 5.03–5.13 (m, 1H), 2.87 (d, J=6.8 Hz, 1H), 2.82 (d, J=6.8 Hz, 1H), 2.65 (br s, 1H), 2.59 (br s, 1H).

Workup

  1. filtrationfiltered
  2. washThe resin was washed with dichloromethane (4×50 mL)
  3. additionThe combined organic solutions were mixed with 20 g of silica gel
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash column chromatography on silica gel with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5a2469008e8f475880f7aa17f056922f
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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