Water → 2-(5-Bromo-3-methoxycarbonyl-phenoxy)-acetic acid tert-butyl ester

HRID 2268567Notes

Reaction equation

HRID 2268567 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Br:11])[CH:5]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[H-].[Na+].O>CN(C=O)C>[C:18]([O:17][C:15](=[O:16])[CH2:14][O:10][C:8]1[CH:7]=[C:6]([Br:11])[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:9]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Product 1

HCID 538044552-(5-Bromo-3-methoxycarbonyl-phenoxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromo-5-hydroxybenzoic acid methyl ester (10.2 g) and tert-butyl bromoacetate (9.7 ml) in anhydrous DMF was added sodium hydride (60% dispersion in mineral oil, 2.69). After 30 min water (10 ml) aws added. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was removed and the organic phase washed with further water, 1M sodium hydroxide solution and dried with brine and over sodium sulphate. Concentration under reduced pressure gave the title compound as dark yellow gum (12.8 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe aqueous phase was removed
  3. washthe organic phase washed with further water, 1M sodium hydroxide solution
  4. dry with materialdried with brine and over sodium sulphate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-eb892a4ae4bf48049f14ea4617a2b85f
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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