4-Bromoaniline → N-(4-Bromophenyl)-3-oxobutanamide

HRID 2112809Notes

Reaction equation

HRID 2112809 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 12661Diketene

Product 1

HCID 598820N-(4-Bromophenyl)-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 25.72 mL (336 mmol) of diketene in 100 mL of toluene is added dropwise at 90° C. to a solution of 51.0 g (288 mmol) of 4-bromoaniline in 200 mL of toluene and the reaction mixture is kept for 5 hours at this temperature. The reaction solution is cooled in the ice bath, and the precipitate formed is filtered and then washed with toluene until the product is virtually colorless. Subsequently it is dried at 50° C. in the circulating air dryer until the weight is constant. Yield: 50.0 g (68% of theoretical); C10H10BrNO2 (M=256.096); calc.: molpeak (M+H)+: 256/258 (Br); found: molpeak (M+H)+: 256/258 (Br); HPLC-MS: 4.7 min (method B).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered
  3. washwashed with toluene until the product
  4. customSubsequently it is dried at 50° C. in the circulating air dryer until the weight
  5. custom4.7 min (method B)

Sources & evidence

ORD record
ord-c5ddacf3307643809bb7889ce93f0956
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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