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Hydrogen Peroxide → 3-Bromo-5-chlorobenzene-1,2-diol

HRID 1094796
Notes
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Reaction equation

HRID 1094796 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)C=O.[OH:12]O>[OH-].[Na+]>[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:4]([OH:12])[C:3]=1[OH:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 5196763-Bromo-5-chloro-2-hydroxybenzaldehyde

Product 1

HCID 177610523-Bromo-5-chlorobenzene-1,2-diolYield 99%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a stirred suspension of 3-bromo-5-chloro-2-hydroxybenzaldehyde (49.5 g, 0.21 mol) in 0.5N aqueous NaOH (500 ml, 250 mmol) at 40° C. was added dropwise hydrogen peroxide (21.4 g of a 35% aqueous solution, 220 mmol) over 15 minutes and the resultant mixture stirred for 16 hours. The mixture was cooled to room temperature, diluted with 1N aqueous NaOH (200 ml) and washed with diethyl ether (3×300 ml). The aqueous layer was acidified with concentrated HCl to pH 2 and extracted with diethyl ether (3×200 ml). The organic extracts were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a red/brown solid (46.0 g, 99% yield).

Workup

  1. washwashed with diethyl ether (3×300 ml)
  2. extractionextracted with diethyl ether (3×200 ml)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-464419be99a749669733399dd9306bb7
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08134007B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes