N-bromobutanimide → N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-acetamide

HRID 1433158Notes

Reaction equation

HRID 1433158 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:11])[CH3:10]>CN(C=O)C.C(Cl)Cl>[C:9]([C:12]1[C:13]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:14][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:16]([Br:1])[CH:17]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 69059816HCID 69059816, compound

Product 1

HCID 69059837N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-acetamideYield 67.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (0.756 g, 4.27 mmol) was added portionwise to a solution of N-(4-acetyl-3-benzyloxy-phenyl)-acetamide (1.2 g, 4.24 mmol) in DMF (24 ml) and the reaction stirred overnight at room temperature. The reaction mixture was diluted with DCM, washed with water and dried over MgSO4 to afford a white solid (1.03 g, 67%). LC/MS: RT=2.609 min. 362/364 (MH+).

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9d97553c2d624c769969abffaf78e1f5
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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