Potassium Carbonate → HCID 68645433, compound

HRID 1161339Notes

Reaction equation

HRID 1161339 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 68645433HCID 68645433, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-fluoro-4-nitrophenol (1.57 g, 10 mmol) in N,N-dimethylformamide (10 ml) were added tert-butyl bromoacetate (1.95 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol). The mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure and the residue purified by column chromatography on silica gel (50 g, dichloromethane eluant) to afford the product as a pale-yellow solid (2.22 g, 84%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by column chromatography on silica gel (50 g, dichloromethane eluant)

Sources & evidence

ORD record
ord-61a9edba3a1042e5afc669f38f392433
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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