Water → HCID 54473706, compound

HRID 2121142Notes

Reaction equation

HRID 2121142 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Li+].[Br-].P(Br)(Br)[Br:23].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:23])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 54007671HCID 54007671, compound

Product 1

HCID 54473706HCID 54473706, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution in DMF (10 mL) of 4-hydroxymethyl-2-phenoxybenzoic acid methyl ester (2.82 g), prepared as in Example 157C, was added LiBr (1.04 g) and PBr3 (3.65 g) and the reaction mixture was stirred for 20 minutes at ambient temperature. The reaction mixture was poured into water and extracted with toluene. The organic phase was washed twice with water, dried over Na2SO4, filtered, and concentrated in vacuo to give 4-bromomethyl-2-phenoxybenzoic acid methyl ester (3.37 g).

Workup

  1. extractionextracted with toluene
  2. washThe organic phase was washed twice with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a30cd49e9e914d2db65a04ca8079ad07
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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