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

HRID 1433167Notes

Reaction equation

HRID 1433167 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:20]=[CH:19][C:18]=1[C:31](=[O:34])[CH2:32][Br:33])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]([Br:1])=[CH:19][C:18]=1[C:31](=[O:34])[CH2:32][Br:33])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579348191-(2,4-Bis-benzyloxyphenyl)-2-bromo-ethanone

Product 1

HCID 579348211-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2-bromo-ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-bromo succinimide (2.67 g, 0.015 mol) was added to a stirred solution of crude 1-(2,4-Bis-benzyloxyphenyl)-2-bromo-ethanone (ca. 6.16 g, 0.015 mol) in dimethylformamide (50 ml) and the mixture was stirred for 18 h. The mixture was concentrated to dryness, dissolved in dichloromethane (50 mL) and washed with (2×50 ml). The combined organic phases were dried over magnesium sulphate and concentrated to give 1-(2,4-Bis-benzyloxy-5-bromo-phenyl)-2-bromo-ethanone as a white solid, which was used without further purification.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutiondissolved in dichloromethane (50 mL)
  3. washwashed with (2×50 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54661084c1684e0da7334664ae8aaeab
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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