N-bromobutanimide → HCID 20330252, compound

HRID 2057755Notes

Reaction equation

HRID 2057755 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH:9]([O:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)[C:10](=[O:15])[C:11]([CH3:12])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 20330256HCID 20330256, compound

Product 1

HCID 20330252HCID 20330252, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 10.5 g (0.046 mole) of 1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone, prepared above, and 8.37 g (0.047 mole) N-bromosuccinimide (NBS) in 300 ml. carbon tetrachloride, with stirring, was irradiated and heated with a sunlamp until all of the NBS was consumed (about 45 min.). The reaction mixture was cooled, filtered, and the filtrate washed with aqueous sodium bisulfite and dried. After removal of the solvent, there was obtained a quantitative yield of 1-bromo-1-(5-chloro-2-pyridinyl-oxy)-3,3-dimethyl-2-butanone, a light yellow oil.

Workup

  1. customwas irradiated
  2. customwas consumed (about 45 min.)
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washthe filtrate washed with aqueous sodium bisulfite
  6. customdried
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-fae2b7151896405191bcce88354888c3
Source dataset
uspto-grants-1980_07
Patent number
US04212869

Reaction notes

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