Methyl 3-bromo-5-(hydroxymethyl)benzoate → Methyl 3-bromo-5-formylbenzoate

HRID 1845296Notes

Reaction equation

HRID 1845296 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][OH:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]>[O-2].[Mn+4].[O-2].C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Product 1

HCID 11436457Methyl 3-bromo-5-formylbenzoate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-bromo-5-(hydroxymethyl)benzoate (149 mg, 0.61 mmol) and manganese(IV) oxide (529 mg, 6.08 mmol), and CH2Cl2 (3 mL) was stirred at rt overnight. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to afford the title compound.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with CH2Cl2
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-793d0a7a5b774a75b219fe3f770c25ed
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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