Benzoyl Peroxide → HCID 90384211, compound

HRID 928660Notes

Reaction equation

HRID 928660 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.BrN1[C:19](=[O:20])CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][O:20][CH3:19])[C:6]=2[C:5]([F:12])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 90384266HCID 90384266, compound

Product 1

HCID 90384211HCID 90384211, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To the compound (49.4 mg, 0.200 mmol) of Step 1 of Example 21, N-bromosuccinimide (hereinafter, NBS) (39.2 mg, 0.220 mmol), and a catalytic amount of benzoyl peroxide (hereinafter, BPO), carbon tetrachloride (2 mL) was added, and heated under reflux overnight. After the resultant was returned to room temperature, the insoluble material was filtered off. The solvent was distilled away under reduced pressure. The resulting residue was dissolved in methanol (2 mL), and a 25% sodium methoxide methanol solution (0.2 mL) was added thereto and heated under reflux for 3 hours. The resultant was returned to room temperature, and the solvent was distilled away under reduced pressure. To the resulting residue, 1 N hydrochloric acid (1 mL) and a saturated aqueous ammonium chloride solution were added, and extraction was performed with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure. The resulting residue was purified by silica gel chromatography to thus obtain the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. customwas returned to room temperature
  4. filtrationthe insoluble material was filtered off
  5. distillationThe solvent was distilled away under reduced pressure
  6. dissolutionThe resulting residue was dissolved in methanol (2 mL)
  7. additiona 25% sodium methoxide methanol solution (0.2 mL) was added
  8. temperatureheated
  9. temperatureunder reflux for 3 hours
  10. customwas returned to room temperature
  11. distillationthe solvent was distilled away under reduced pressure
  12. additionTo the resulting residue, 1 N hydrochloric acid (1 mL) and a saturated aqueous ammonium chloride solution were added
  13. extractionextraction
  14. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  15. distillationThe solvent was distilled away under reduced pressure
  16. customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9cd333d03e914e8291a2f3b2a323935a
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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