4-Chloro-2-nitrophenol → HCID 22997608, compound

HRID 1166220Notes

Reaction equation

HRID 1166220 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:9]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([CH2:14][CH:13]=[CH2:12])[C:5]=1[OH:8])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 69804-Chloro-2-nitrophenolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 22997608HCID 22997608, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-chloro-2-nitrophenol (100 g), allyl bromide (69.7 g), and potassium carbonate (95.5 g) in acetone (1 L) was refluxed for 6 hours. After cooling to room temperature and filtration, the filtrate was concentrated to give a residue. The residue was extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo to give a crude product (110.9 g, 90%) which was used in the next step without purification. 42 g of the crude product was heated at 180° C. for 8 hours. Purification by flash chromatography over silica gel (elution with 50% ethyl acetate in hexanes) gave 22 g (50%) of 2-nitro-4-chloro-6-allylphenol. 1H NMR (300 MHz, CDCl3) δ8.00 (d, J=2.6 Hz, 1 H), 7.44 (d, J=2.6 Hz, 1 H), 6.00-5.89 (m, 1 H), 5.20-5.12 (m, 2 H), 3.48 (d, J=6.69 Hz, 2 H).

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationfiltration
  3. concentrationthe filtrate was concentrated
  4. customto give a residue
  5. extractionThe residue was extracted with dichloromethane
  6. washThe organic layer was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customto give a crude product (110.9 g, 90%) which
  10. customwas used in the next step without purification
  11. temperature42 g of the crude product was heated at 180° C. for 8 hours
  12. customPurification by flash chromatography over silica gel (elution with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-74b889f2101b4906ba87c617e05cb2f3
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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