Benzoyl Peroxide → HCID 15837892, compound

HRID 1081863Notes

Reaction equation

HRID 1081863 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)=[C:4]([CH3:19])[CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:19][C:4]1[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 23363133HCID 23363133, compound

Product 1

HCID 15837892HCID 15837892, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-(4-Chloro-2-methylphenoxy)naphthalene (1.8 g) from Example 1 was dissolved in carbon tetrachloride (10 ml), followed by addition of NBS (1.2 g) and a catalytic amount of benzoyl peroxide under reflux for 2 hours. After leaving the solution to stand at room temperature, insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ether=99:1) to give the title compound (900 mg; 39%).

Workup

  1. customAfter leaving the solution
  2. customto stand at room temperature
  3. filtrationinsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (hexane:ether=99:1)

Sources & evidence

ORD record
ord-e6c014ebebac4497a8f2c7e8947cad12
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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