N-bromobutanimide → HCID 13902401, compound

HRID 1165440Notes

Reaction equation

HRID 1165440 reaction equation
[OH:1][C:2]1[C:9]([Br:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][CH3:14])[C:3]=1[CH:4]=[O:5].[Br:15]N1C(=O)CCC1=O>C(O)(=O)C.O>[OH:1][C:2]1[C:9]([Br:10])=[C:8]([O:11][CH3:12])[C:7]([Br:15])=[C:6]([O:13][CH3:14])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19861824HCID 19861824, compound

Product 1

HCID 13902401HCID 13902401, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.0 g (3.83 mmol) of 2-hydroxy-3-bromo-4,6-dimethoxybenzaldehyde (see R. Royer, et al, Eur. J. Med. Chem., 12:455 (1977) as an example of how to obtain this material) in 50 ml of glacial acetic acid was warmed to 60° C. N-Bromosuccinimide (0.68 g, 3.83 mmol) was added in one portion and the solution was cooled to ambient temperature. The reaction mixture was diluted with 200 ml of water and the solids were filtered and air dried. The solid was crystallized from ethanol. There was obtained 1.1 g (3.24 mmol, 84%) of 2-hydroxy-3,5-dibromo-4,6-dimethoxybenzaldehyde as a white solid; mp 103°-104° C.

Workup

  1. temperaturethe solution was cooled to ambient temperature
  2. filtrationthe solids were filtered
  3. customair dried
  4. customThe solid was crystallized from ethanol

Sources & evidence

ORD record
ord-edbd4515c6644536b357d6362699481c
Source dataset
uspto-grants-1990_03
Patent number
US04910202

Reaction notes

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