Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

HRID 2427581Notes

Reaction equation

HRID 2427581 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].[Br:12]NC(=O)CCC(N)=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:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][Br:12]

Participants

5

Reactant 2

HCID 33094Methyl o-toluateHCID 9834204N-Bromosuccinamide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 87.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-methyl-benzoic acid methyl ester (1.53 g, 10 mmol), N-bromosuccinamide (1.95 g, 11 mmol), and benzoyl peroxide (0.056 g, 0.21 mmol) in carbon tetrachloride (20 mL) was heated at reflux until the starting materials were mostly consumed. Workup and silica gel column chromatography using 5% ethyl acetate in hexane afforded 2-bromomethyl-benzoic acid methyl ester (2.0 g, 87%). GC-MS: m/z 230 (M1)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until the starting materials
  3. customwere mostly consumed

Sources & evidence

ORD record
ord-69a89e07fba14542aa99289526d653ed
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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