Benzoyl Peroxide → HCID 19390097, compound

HRID 1042357Notes

Reaction equation

HRID 1042357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].C1C(=O)N([Br:18])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 134345771-Chloro-2-methoxy-3-methylbenzene

Product 1

HCID 19390097HCID 19390097, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-chloro-2-methoxy-3-methyl-benzene (13.40 g, 85.60 mmol), NBS (15.30 g, 86.00 mmol) and a catalytic amount of benzoyl peroxide (150 mg) in CCl4 was refluxed for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The precipitate was washed with pentane. The solvent was distilled off and the residue was purified by column chromatography using pentane as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 4.00 (s, 3H), 4.56 (s, 2H), 7.04 (t, J=7.62 Hz, 1H), 7.29 (dd, J=7.62 Hz, 1H), 7.34 (dd, J=7.92 Hz, 1H).

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with pentane
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-91e223c0fc3f4945ad1067a96e327316
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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