Water → 1-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone

HRID 1891154Notes

Reaction equation

HRID 1891154 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23](=[O:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:26]N1C(=O)CCC1=O.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:12]([Br:26])=[CH:11][C:10]=1[C:23](=[O:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanone

Product 1

HCID 247744411-(2,4-Bis-benzyloxy-5-bromo-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

51.2 g of 1-(2,4-Bis-benzyloxy-phenyl)ethanone (0.154 mol, 1 eq) were dissolved in 250 ml DMF. 27.42 g N-bromosuccinimide (0.154 mol, 1 eq) in 100 ml DMF were added dropwise. The mixture was stirred at room temperature over night. The reaction mixture was poured onto 700 ml of water and the precipitate filtered off. The filter cake was rinsed with water and the colourless solid was recrystallised from 370 ml acetonitrile.

Workup

  1. filtrationthe precipitate filtered off
  2. washThe filter cake was rinsed with water
  3. customthe colourless solid was recrystallised from 370 ml acetonitrile

Sources & evidence

ORD record
ord-130b7b61dbdf4b4e90f7b85974eb3a98
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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