Benzoyl Peroxide → 2-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

HRID 337619Notes

Reaction equation

HRID 337619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]=1[CH3:13].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:13][C:3]1[CH:4]=[C:5]([O:8][CH2:9][CH2:10][O:11][CH3:12])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22467254HCID 22467254, compound

Product 1

HCID 591775552-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1-chloro-4-(2-methoxyethoxy)-2-methylbenzene (1 eq.) from the previous step, NBS (1.1 eq.) and benzoyl peroxide (0.05 eq.) in CCl4 (0.2 M) was refluxed for 2 h. The volatiles were then removed in vacuo and the resulting residue was suspended in hexanes. The insolubles were removed via filtration and washed further with hexanes. The filtrate was concentrated in vacuo to afford the title compound as a colorless oil.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe volatiles were then removed in vacuo
  3. customThe insolubles were removed via filtration
  4. washwashed further with hexanes
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-34047ed8e1f54db7a6d2fbe6d7aa3373
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…