4-Nitrophenol → HCID 69066270, compound

HRID 1987823Notes

Reaction equation

HRID 1987823 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH3:17][CH2:18][O:19][C:20]([CH3:22])=[O:21]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:22]2[CH2:17][CH2:18][O:19][C:20]2=[O:21])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 69066270HCID 69066270, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitrophenol (278 mg, 2.0 mmol) in DMF (6 mL) at room temperature under a nitrogen atmosphere was added powdered K2CO3 (552 mg, 2.0 mmol) followed by3-bromo-dihydrofuran-2-one (330 mg, 2.0 mmol). After stirring at room temperature under a nitrogen atmosphere for 16 hours, the mixture was diluted to 30 mL with EtOAc and washed with water (4×30 mL) and brine (30 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to provide the product (240 mg, 54%) as tan oil that later solidified.

Workup

  1. washwashed with water (4×30 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7db77c03c34148cfb99f42c9f483dc50
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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