4'-Bromoacetanilide → N-(4-bromo-2-fluorophenyl)acetamide

HRID 373678

Reaction equation

HRID 373678 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[O-]S(C(F)(F)[F:17])(=O)=O.F[N+]1C=CC=CC=1>ClC(Cl)CCl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[F:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 76834'-BromoacetanilideHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)

Product 1

HCID 67593N-(4-bromo-2-fluorophenyl)acetamideYield 28%

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.17 g (5.0 mmol) of N-acetyl-4-bromoaniline, 1.20 g (5.0 mmol) of N-fluoropyridinium triflate, and 50 ml of 1,1,2-trichloroethane was placed in a 100 ml 3-necked round bottomed flask equipped with a magnetic stirring bar, a thermometer, and a reflux condenser. The mixture was heated to 100° C. and allowed to react at that temperature for 20 hours. The mixture was then allowed to cool and the volatiles were removed by evaporation under reduced pressure. Analysis of the residue by standardized gas-liquid chromatography using a mass spectrometer detector indicated that the title product was present in 28 percent yield and that the balance of the N-acetyl-4-bromoaniline was still present as unreacted material.

Workup

  1. customwas placed in a 100 ml 3-necked round bottomed flask
  2. customequipped with a magnetic stirring bar
  3. customto react at that temperature for 20 hours
  4. temperatureto cool
  5. customthe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9c2faacbfe2e4ec3bac22144d3f63261
Source dataset
uspto-grants-1992_11
Patent number
US05164502

Linked notes

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