N-bromobutanimide → HCID 22556911, compound

HRID 983799Notes

Reaction equation

HRID 983799 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=1>CN(C=O)C>[Br:1][C:13]1[C:14]([OH:20])=[C:15]([C:17](=[O:19])[CH3:18])[CH:16]=[C:11]([CH2:10][Cl:9])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22557013HCID 22557013, compound

Product 1

HCID 22556911HCID 22556911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (10 mmol) in 8 mL of DMF is added dropwise to a solution of 1-(5-chloromethyl-2-hydroxy-phenyl)-ethanone 211 (10 mmol) in 20 mL DMF and the resulting mixture is stirred for 12-18 h. The solvent is evaporated under reduced pressure and the residue is diluted with water resulting in the formation of a solid. The solid is isolated and recrystallized from ethanol to yield 1-(3-Bromo-5-chloromethyl-2-hydroxy-phenyl)-ethanone 212.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. additionthe residue is diluted with water resulting in the formation of a solid
  3. customThe solid is isolated
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-cead4e0bfdaf449f9704e72a4b75ca5f
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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