N-bromobutanimide → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 1869409Notes

Reaction equation

HRID 1869409 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:11])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

Product 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzeneYield 97.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
105 °C

Procedure

57 g (363.96 mmol) of 2-chloro-5-methylanisole is dissolved in 800 ml of carbon tetrachloride and mixed at room temperature with 69.9 g (393.08 mmol) of N-bromosuccinimide. After 174.6 mg of benzoyl peroxide is added, it is refluxed for five hours (bath temperature 105° C.). The reaction mixture is suctioned off through a glass-pleated filter, rewashed, and the solution is spun in a rotary evaporator. 83.6 g (97.5%) of the desired product (COntains traces of starting material and dibromide) is obtained, which is incorporated in crude form into the next stage.

Workup

  1. customthe solution is spun in a rotary evaporator

Sources & evidence

ORD record
ord-dfce6d849b034bbe96b4feee2fa7acda
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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