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

HRID 1784202Notes

Reaction equation

HRID 1784202 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.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>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 749781,1'-Azobis(cyclohexanecarbonitrile)

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methyl-benzoic acid methyl ester (4.58 g, 30.5 mmol) in CCl4 (75 mL) was added N-bromosuccinimide (5.79 g, 32.5 mmol) followed by 1,1′-azobis(cyclohexanecarbonitrile) (1.42 g, 5.80 mmol). The resultant mixture was refluxed for 6 hours then cooled to room temperature, filtered through filter paper, and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:hexanes-EtOAc) provided 5.44 g (78%) of 2-bromomethyl-benzoic acid methyl ester as a colorles oil. 1H NMR (CDCl3) δ 3.95 (s, 3H), 4.96 (s, 2H), 7.36-7.50 (m, 3H), 7.97 (d, 1H, J=7.8 Hz).

Workup

  1. filtrationfiltered
  2. filtrationthrough filter paper
  3. concentrationconcentrated
  4. customPurification of the crude material by column chromatography on silica gel (20:1:hexanes-EtOAc)

Sources & evidence

ORD record
ord-5b98b66900a94a9a9fc3531729dcd456
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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