N-bromobutanimide → 2-Amino-5-bromo-4-methoxybenzaldehyde

HRID 524072

Reaction equation

HRID 524072 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>ClCCl>[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

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3235032-Amino-4-methoxybenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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). LCMS monitored the reaction until the starting material consumed completely. 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. customthe reaction until the starting material
  2. customconsumed completely
  3. additionThe reaction mixture was diluted with dichloromethane and water
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-155398206c3b4298ade26f276c7a08a2
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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