Ethyl Nitrite → 2'-Bromo-6'-trifluoromethylacetanilide

HRID 1283786Notes

Reaction equation

HRID 1283786 reaction equation
S(O)(O)(=O)=O.N[C:7]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[C:9]([Br:21])[CH:8]=1.N(OCC)=O>[Cu].O>[Br:21][C:9]1[CH:8]=[CH:7][CH:16]=[C:15]([C:17]([F:18])([F:20])[F:19])[C:10]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 2

HCID 8026Ethyl NitriteHCID 681430314'-Amino-2'-bromo-6'-trifluoromethylacetanilide sulfate

Product 1

HCID 232538532'-Bromo-6'-trifluoromethylacetanilide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a suspension of 4'-amino-2'-bromo-6'-trifluoromethylacetanilide sulfate is added two molar equivalents of ethyl nitrite. The reaction mixture is cooled (0°) and stirred for 2 hours then allowed to warm to 25° and a catalytic amount of copper bronze is added. The mixture is stirred for 3 hours with the temperature maintained below 40°. The mixture is then refluxed briefly and cooled. Addition of water gives 2'-bromo-6'-trifluoromethylacetanilide which is collected by filtration.

Workup

  1. temperatureThe reaction mixture is cooled (0°)
  2. temperatureto warm to 25°
  3. stirringThe mixture is stirred for 3 hours with the temperature
  4. temperaturemaintained below 40°
  5. temperatureThe mixture is then refluxed briefly
  6. temperaturecooled

Sources & evidence

ORD record
ord-dd4655ba82d6419181b51500ae1e787d
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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