Sodium Sulfate → 2-Amino-5-bromo-4-methoxybenzaldehyde

HRID 56482

Reaction equation

HRID 56482 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:12]N1C(=O)CCC1=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([Br:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 67184N-bromobutanimideHCID 3235032-Amino-4-methoxybenzaldehyde

Product 1

HCID 593252582-Amino-5-bromo-4-methoxybenzaldehydeYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-amino-4-methoxybenzaldehyde (6 g, 39.7 mmol) in dichloromethane (100 mL) was added N-bromosuccinimide (7 g, 39.7 mmol). The reaction mixture was diluted with dichloromethane and water. The separated organic layer was dried sodium sulfate, filtered and concentrated to give the title compound (5 g, 56%) as a yellow solid. MS (ES+) C8H8BrNO2 requires: 229, 231, found: 230, 232 [M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1203a7025ae741efb01dce4fb28ead02
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Linked notes

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