N-bromobutanimide → Methyl 2-(bromomethyl)-4-methoxybenzoate

HRID 1761006Notes

Reaction equation

HRID 1761006 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH3:12].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][Br:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13257269Methyl 4-methoxy-2-methylbenzoate

Product 1

HCID 139928Methyl 2-(bromomethyl)-4-methoxybenzoateYield 58%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 4-methoxy-2-methyl-benzoic acid methyl ester (20 g, 111 mmol), N-bromosuccinimide (20.7 g, 117 mmol) and dibenzoylperoxide (0.54 g, 2 mmol) in CCl4 (150 mL) was irradiated with a 300 W lamp. The reaction maintains a steady reflux and after 4.5 h, the lamp was removed and the mixture cooled to 5° C. The mixture was then filtered, the filtrate evaporated and the residue purified twice by chromatography (SiO2, Heptane:Diethyl ether: 95:5 to 85:15) to afford the title product (16.6 g, 58%) as a white solid. MS m/e=258.1 (M−H+).

Workup

  1. customwas irradiated with a 300 W lamp
  2. temperaturea steady reflux and after 4.5 h
  3. customthe lamp was removed
  4. filtrationThe mixture was then filtered
  5. customthe filtrate evaporated
  6. customthe residue purified twice by chromatography (SiO2, Heptane:Diethyl ether: 95:5 to 85:15)

Sources & evidence

ORD record
ord-43ca25cacd55454da92f4e8a1935796e
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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