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

HRID 594965Notes

Reaction equation

HRID 594965 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:11])=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.ClCCl>[Br:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 2

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl-o-toluate (0.93 mL, 6.6 mmol), N-bromosuccinimide (1.25 g, 7.0 mmol) and azaisobutryonitrile (11 mg, 0.07 mmol) in chloroform (10 mL) was heated at 65° for 16 h. After cooling to rt, the mixture was diluted with dichloromethane and washed with H2O and then brine. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give methyl 2-(bromomethyl)benzoate.

Workup

  1. washwashed with H2O
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bed9197b69cb43d5b962983715b90453
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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