2-Amino-5-bromobenzenemethanol → 2-Amino-5-bromobenzaldehyde

HRID 2404016Notes

Reaction equation

HRID 2404016 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][OH:10]>C(Cl)Cl.O=[Mn]=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]=[O:10]

Participants

4

Reactant 1

HCID 110308742-Amino-5-bromobenzenemethanol

Product 1

HCID 235104752-Amino-5-bromobenzaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81%), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199. found: 200, 202 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ef16690ef44240feac90807a299b1a2d
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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