Hydrogen Peroxide → 4-Bromocatechol

HRID 1423095Notes

Reaction equation

HRID 1423095 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)C=O.[OH:11]O>[OH-].[Na+]>[Br:1][C:2]1[CH:9]=[C:6]([OH:11])[C:5]([OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 728635-Bromosalicylaldehyde

Product 1

HCID 284874-BromocatecholYield 74%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-bromo-2-hydroxybenzaldehyde (10 g, 50 mmol) was dissolved in a 1 N aqeuous NaOH solution (55 mL). To this yellow solution was added hydrogen peroxide (36%, 12 mL) dropwise via addition funnel at room temperature. After stirring for 2 h, the reaction was quenched by adding saturated solution of Na2S2O3, and extracted with EtOAc. The organic extract was washed with 1N HCl, water, brine, and passed through a short pad of silica gel to obtain 4-bromobenzene-1,2-diol (7.0 g, 74%) as a brown solid. 1H NMR (300 MHz, CDCl3) 7.02 (d, J=2.1, 1H), 6.91 (dd, J=8.8, 2.1, 1H), 6.73 (d, J=8.8, 1H).

Workup

  1. additiondropwise via addition funnel at room temperature
  2. customthe reaction was quenched
  3. additionby adding saturated solution of Na2S2O3
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with 1N HCl, water, brine

Sources & evidence

ORD record
ord-14e3a65f1cdc462d93c211bf86eb85d6
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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