(2-Amino-5-bromo-3-methoxyphenyl)methanol → 2-Amino-5-bromo-3-methoxybenzaldehyde

HRID 2079613Notes

Reaction equation

HRID 2079613 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Br:10])=[CH:4][C:3]=1[CH2:11][OH:12]>[O-2].[O-2].[Mn+4].C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([Br:10])=[CH:4][C:3]=1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 46738297(2-Amino-5-bromo-3-methoxyphenyl)methanol

Product 1

HCID 153804452-Amino-5-bromo-3-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a 0.15 M chloroform solution of (2-amino-5-bromo-3-methoxyphenyl)methanol (10.16 g, 43.96 mmol) was added manganese dioxide (19.9 g, 280.5 mmol). The mixture was stirred under argon at room temperature for 16 hours. The resulting mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated to dryness and used in next step. ES/MS m/z 228/230 (MH+).

Workup

  1. filtrationThe resulting mixture was filtered through celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a787d7f738f7444da2f3c19340e0899f
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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