N-bromobutanimide → HCID 18995940, compound

HRID 37583Notes

Reaction equation

HRID 37583 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][C:8]([CH:15]([Cl:20])[C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[C:10]2[O:9][C:8]([CH:15]([Cl:20])[C:16]([F:19])([F:18])[F:17])([C:11]([F:12])([F:13])[F:14])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18995939HCID 18995939, compound

Product 1

HCID 18995940HCID 18995940, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

64 g of 4-methyl-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 9 were dissolved in 500 ml of carbon tetrachloride, and 36 g of N-bromosuccinimide and 0.5 g of AIBN (azoisobutyronitrile) were added. The mixture was stirred under reflux for 3 hours and then cooled and filtered. The solvent was stripped off and the residue was distilled under vacuum. The yield was 57 g (71% of theory) and the boiling point was 80°-82° C. at 0.1 mbar. The NMR spectrum showed the following characteristic absorption: 1H NMR: 4.72 ppm.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. distillationthe residue was distilled under vacuum
  5. customthe following characteristic absorption

Sources & evidence

ORD record
ord-0fbb6fd99c8c41b29de00464f90366df
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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