N-(2-Acetylphenyl)acetamide → N-(2-acetyl-4-bromophenyl)acetamide

HRID 711387

Reaction equation

HRID 711387 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].[Br:14]Br>CC(O)=O>[C:1]([C:4]1[CH:9]=[C:8]([Br:14])[CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 21306N-(2-Acetylphenyl)acetamideHCID 24408Bromine

Product 1

HCID 459291N-(2-acetyl-4-bromophenyl)acetamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under N2, a pale yellow suspension of crude N-(2-acetylphenyl)acetamide (28 g, 158 mmol) in AcOH (300 mL) was stirred for about 5 min, and Br2 (12.95 mL, 253 mmol) was added within 1 h at room temperature. The resulting mixture was then stirred at room temperature for 75 min. After the reaction went to completion as monitored by LC-MS, the reaction mixture was quenched with H2O (200 mL). The mixture was filtered through Buchner funnel, and the solid was collected as N-(2-acetyl-4-bromophenyl)acetamide (35 g, yield 86%). MS (m/z): 216 (M+H)+.

Workup

  1. stirringThe resulting mixture was then stirred at room temperature for 75 min
  2. customthe reaction mixture was quenched with H2O (200 mL)
  3. filtrationThe mixture was filtered through Buchner funnel

Sources & evidence

ORD record
ord-9b630fec78ce435691e5aa86e1ea7c20
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Linked notes

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