Benzoyl Peroxide → 2-(Bromomethyl)-1-chloro-3-methoxybenzene

HRID 629993

Reaction equation

HRID 629993 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH3:10].[Br:11]N1C(=O)CCC1=O.C1(C(OOC(=O)C2C=CC=CC=2)=O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:10][C:3]1[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 767493-Chloro-2-methylanisole

Product 1

HCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a 250 mL round bottom flask, 1-chloro-3-methoxy-2-methylbenzene (5.0 g, 31.9 mmol) was dissolved in CCl4 (50 mL). To the solution, 1-bromopyrrolidine-2,5-dione (5.8 g, 32.6 mmol) and benzoyl benzenecarboperoxoate (70 mg) were added in sequence. The resulting mixture was refluxed for 4 hours and left at room temperature overnight. The mixture was filtered. The filtrate was evaporated to provide crude product of 2-(bromomethyl)-1-chloro-3-methoxybenzene as a colorless liquid, which was used for next step without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. filtrationThe mixture was filtered
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-41b966ef37fc49338ddd208e4d4c6619
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Linked notes

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