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

HRID 2274177Notes

Reaction equation

HRID 2274177 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-27fcbb4795124848b09028b61531077b
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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