Sodium Chloride → Methyl 2-bromo-2-(2-methoxyphenyl)acetate

HRID 1982175Notes

Reaction equation

HRID 1982175 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=1[CH:9](O)[C:10]([O:12][CH3:13])=[O:11].[Na+].[Cl-]>>[Br:2][CH:9]([C:8]1[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=1[O:6][CH3:5])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 24614Phosphorus tribromideHCID 586311Methyl 2-hydroxy-2-(2-methoxyphenyl)acetate

Product 1

HCID 14234296Methyl 2-bromo-2-(2-methoxyphenyl)acetateYield 96.6%

Procedure

146.6 ml (1.57 moles) of phosphorus tribromide are added dropwise to 109.7 g (0.562 mole) of methyl 2-methoxymandelate, while cooling well. After 3 hours stirring at room temperature, the mixture is poured into 3N NaCl solution, and extracted with methylene chloride. After washing the organic phase with water, it is dried with Na2SO4 and is concentrated. 140.7 g of the title compound are obtained as a yellowish oil which is used further without purification.

Workup

  1. temperaturewhile cooling well
  2. extractionextracted with methylene chloride
  3. washAfter washing the organic phase with water, it
  4. dry with materialis dried with Na2SO4
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-c04fbf351f03452b92a3d758564cdaf8
Source dataset
uspto-grants-1986_06
Patent number
US04595685

Reaction notes

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