Bromine → N-(2-bromo-4-tert-butylphenyl)acetamide

HRID 1377111Notes

Reaction equation

HRID 1377111 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][C:6]=1[Br:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 140672p-t-Butylacetanilide

Product 1

HCID 258026N-(2-bromo-4-tert-butylphenyl)acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 20.80 g (108.7 mmol) of N-acetyl-4-tert-butyl aniline and 0.33 g (2 mmol) of ferric chloride in 70 ml of acetic acid is added dropwise 17.9 g (112 mmol) of bromine while the temperature is kept between 30° C. and 40° C. Then the reaction mixture is stirred 4 hours and poured into 500 ml of ice water. The precipitate is filtered off, washed with water and recrystallized from 70% ethanol. Thus is obtained 24.33 g (83%) of title compound.

Workup

  1. customis kept between 30° C. and 40° C
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customrecrystallized from 70% ethanol

Sources & evidence

ORD record
ord-c086373315e447738124cdac64438b62
Source dataset
uspto-grants-1997_09
Patent number
US05663448

Reaction notes

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