Bromine → N-[4-(Bromoacetyl)phenyl]benzamide

HRID 980185Notes

Reaction equation

HRID 980185 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19]Br>C(Cl)(Cl)Cl>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:18])[CH2:17][Br:19])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 223354N-(4-Acetylphenyl)benzamide

Product 1

HCID 12537708N-[4-(Bromoacetyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A warm solution of 4'-benzamidoacetophenone (1.031 g) in chloroform (100 ml) was treated with bromine (0.22 ml). After dilution with more chloroform (50 ml), the resulting solution was washed with 2N-sodium hydroxide solution (2×25 ml) and water (50 ml), dried (MgSO4) and evaporated to a white solid (1.315 g). This was crystallised from ethanol to give the title acetophenone (922 mg); m.p. 171°-174°.

Workup

  1. washAfter dilution with more chloroform (50 ml), the resulting solution was washed with 2N-sodium hydroxide solution (2×25 ml) and water (50 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to a white solid (1.315 g)
  4. customThis was crystallised from ethanol

Sources & evidence

ORD record
ord-bc83d68808e54fcaa93ab0eeaf8942cc
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Reaction notes

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