Sodium hydride → Methyl [2-(3-Bromo-4-fluorophenoxy)phenyl]oxoacetate

HRID 992744Notes

Reaction equation

HRID 992744 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[CH:8][C:9]=1[F:10].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21]>CS(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[F:10])[O:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27833813-Bromo-4-FluorophenolHCID 10856111Methyl 2-(2-fluorophenyl)-2-oxoacetate

Product 1

HCID 11439593Methyl [2-(3-Bromo-4-fluorophenoxy)phenyl]oxoacetateYield 87.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A suspension of 3.75 g of 80% pure NaH in 50 ml of dimethyl sulfoxide (DMSO) was admixed with 21.7 g of 3-bromo-4-fluorophenol (cf. DE-A 192 80 27) and then stirred at 20-25° C. for 30 min, and a solution of 22.7 g of methyl 2-(2-fluorophenyl)oxoacetate in 100 ml of DMSO was added dropwise. The reaction mixture was stirred at 20-25° C. for approximately 12 hours, poured into ice-water and then extracted with ethyl acetate. The organic phases were washed with 1 N aqueous sodium hydroxide solution and water and dried, and the solvent was distilled off, giving 35 g of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 20-25° C. for approximately 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phases were washed with 1 N aqueous sodium hydroxide solution and water
  4. customdried
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-773ff493fe684e66aebfc9fbf733d7f6
Source dataset
uspto-grants-2002_10
Patent number
US06469195B1

Reaction notes

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