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

HRID 1857571Notes

Reaction equation

HRID 1857571 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]N1C(=O)CCC1=O.C(OCC)(=O)C.CCCCCC>C(Cl)(Cl)(Cl)Cl>[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 3

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexane

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 102.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl-2-methylbenzoate (3.00 g, 20.0 mmol) in carbon tetrachloride (15 mL) was added N-Bromosuccinimide (3.55 g, 20.00 mmol). The reaction was allowed to stirr at reflux for 3 h. The mixture was cooled and then partioned between 1:1 ethyl acetate/hexane and the combine organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure afforded the title compound as a yellowish liquid (4.70 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.98 (d, 1H), 7.54-7.35 (mm, 3H), 4.98 (s, 2H), 3.98 (s, 3H).

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe mixture was cooled
  3. washthe combine organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ee0b8c0b61394c5b9dd4d685e2c31a2c
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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