Bromine → N-[4-(2-Bromoacetyl)Phenyl]Acetamide

HRID 45666

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:14]Br>C(O)(=O)C>[Br:14][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)=[O:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of N-(4-acetylphenyl)acetamide (1 g, 5.65 mmol, 1.00 equiv) in acetic acid (10 mL). This was followed by the addition of a solution of bromine (910 mg, 5.69 mmol, 1.01 equiv) in acetic acid (2 mL) dropwise with stirring at 50° C. The resulting solution was stirred for 1.5 h at 50° C. The reaction was then quenched by the addition of 100 mL of water/ice. The solids were collected by filtration and dried under vacuum. This resulted in 0.5 g (33%) of N-(4-(2-bromoacetyl)phenyl)acetamide as a white solid.

Workup

customInto a 100-mL 3-necked round-bottom flask, was placed
stirringThe resulting solution was stirred for 1.5 h at 50° C
customThe reaction was then quenched by the addition of 100 mL of water/ice
filtrationThe solids were collected by filtration
customdried under vacuum
customThis resulted in 0.5 g (33%) of N-(4-(2-bromoacetyl)phenyl)acetamide as a white solid

Sources & evidence

ORD record: ord-ba0c0b9a0fc242a0a344dbd86f34d9a5
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541448B2

Linked notes

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