Water → Benzyl 3-bromo-2-(hydroxymethyl)benzoate

HRID 734483Notes

Reaction equation

HRID 734483 reaction equation
[Br:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH2:20]>[OH-].[Na+].CN(C)C=O>[Br:1][C:2]1[C:10]([CH2:9][OH:8])=[C:6]([CH:5]=[CH:4][CH:3]=1)[C:7]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:20]

Participants

6

Reactant 3

HCID 962WaterHCID 7498Benzyl BromideHCID 115937154-Bromo-2-benzofuran-1[3H]-one

Product 1

HCID 66771262Benzyl 3-bromo-2-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-bromo-2-benzofuran-1(3H)-one (4.02 g, 18.9 mmol) in aqueous sodium hydroxide solution (1M, 18.9 ml) was heated at 100° C. for 1 h. The solution was concentrated in vacuo and the residue was dissolved in toluene and re-concentrated. To a solution of the residue in N,N-dimethylformamide (20 ml) was added benzyl bromide (2.26 ml, 18.90 mmol) and the reaction mixture was stirred at room temperature for 14 days. The mixture was poured into water and the resulting precipitate was collected by filtration, washed with water and pentane and dried to give the title compound (4.77 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in toluene
  3. concentrationre-concentrated
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water and pentane
  6. customdried

Sources & evidence

ORD record
ord-f5e419a6d2014b1f9b023024ccf138e0
Source dataset
uspto-grants-2009_09
Patent number
US07592362B2

Reaction notes

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