4-Chlorophenol → HCID 66887528, compound

HRID 926988Notes

Reaction equation

HRID 926988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1([C:14](OCC)=O)[CH2:13][CH2:12][CH2:11]1.[C:19](=[O:22])([O-])[O-:20].[K+].[K+].[CH3:25]N(C=O)C>>[CH2:14]([CH:10]1[CH2:11][CH2:12][C:13]1([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:19]([OH:20])=[O:22])[CH3:25]

Participants

5

Reactant 4

HCID 46844-ChlorophenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 97595Ethyl 1-bromocyclobutanecarboxylate

Product 1

HCID 66887528HCID 66887528, compoundYield 26%

Conditions

Temperature
57.5 °C

Procedure

A mixture of p-chlorophenol (621 mg, 4.83 mmol), ethyl 1-bromocyclobutanecarboxylate (1.0 g, 4.83 mmol) and potassium carbonate (1.33 g, 9.66 mmol) in DMF (14.5 ml) was stirred and heated to about 55-60° C. under a nitrogen atmosphere for about 18 hours. The solvent was removed under high vacuum, the residue was taken up in diethyl ether (50 ml) and was washed with water and brine (15 ml each). The organic layer was dried (MgSO4), and filtered. The solvent was removed under vacuum and the residue was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (2:1) as the mobile phase to provide 320 mg (26%) of the title compound. MS (DCI): m/z 272 (M+NH4)+.

Workup

  1. customThe solvent was removed under high vacuum
  2. washwas washed with water and brine (15 ml each)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-dd423a1776264c90aec6fd7f5c137d4b
Source dataset
uspto-grants-2016_03
Patent number
US09290444B2

Reaction notes

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