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

HRID 1197128Notes

Reaction equation

HRID 1197128 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-430f279f7693433a85e2a37f3851f8d1
Source dataset
uspto-grants-1992_05
Patent number
US05116982

Reaction notes

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