N-bromobutanimide → HCID 22600461, compound

HRID 1760068Notes

Reaction equation

HRID 1760068 reaction equation
[CH3:1][C:2]1[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[N:12]=[C:11]([C:13]([F:15])([F:16])[F:14])[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11564892Ethyl 2-methyl-6-(trifluoromethyl)nicotinate

Product 1

HCID 22600461HCID 22600461, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
15 °C

Procedure

434.4 g (1.866 mol) of ethyl 2-methyl-6trifluoromethylnicotinate (preparation similar to Heterocycles 129, 46, 1997) and 398.5 g (2.239 mol) of N-bromosuccinimide in 3 500 ml of carbon tetrachloride in the presence of 30.6 g (0.1866 mol) of α,α-azaisobutyronitrile are heated at 75° C., with irradiation from a 150 Watt lamp. After 3 hours, the reaction is terminated, the mixture is cooled to 15° C. and precipitated succinimide is removed by filtration. After evaporation of the solvent, the residue is distilled under reduced pressure. This gives ethyl 2-bromomethyl-6-trifluoromethylnicotinate as an oily product (260.2 g, 44.7% of theory, b.p. 74° C./0.04 mmHg).

Workup

  1. customthe reaction is terminated
  2. customprecipitated succinimide
  3. customis removed by filtration
  4. customAfter evaporation of the solvent
  5. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-eb5e45ca00d6437fbb96738c3fdfca50
Source dataset
uspto-grants-2005_01
Patent number
US06838564B2

Reaction notes

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