N-bromobutanimide → HCID 90384261, compound

HRID 928666Notes

Reaction equation

HRID 928666 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH3:11])[C:6]=2[C:5]([F:12])=[C:4]([F:13])[CH:3]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][Br:21])[C:6]=2[C:5]([F:12])=[C:4]([F:13])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 90384266HCID 90384266, compound

Product 1

HCID 90384261HCID 90384261, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

the compound (2.6 g, 10.5 mmol) of Step 1 of Example 21, NBS (2.06 g, 11.58 mmol), BPO (catalytic amount), and carbon tetrachloride (120 mL) were added, and heated under reflux overnight. After cooling, the solvent was distilled away. After diluted with ethyl acetate, the resultant was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away, and the resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled away
  5. additionAfter diluted with ethyl acetate
  6. washthe resultant was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away
  9. customthe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-83e60845733a40e3a2bfe6bc8fe357fb
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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