Bromine → Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

HRID 1591137Notes

Reaction equation

HRID 1591137 reaction equation
[Br:1]Br.[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8]>ClC(Cl)(Cl)Cl>[CH3:3][O:4][N:5]=[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][Br:1])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 54500888Methyl 2-(methoxyimino)-2-(2-methylphenyl)acetate

Product 1

HCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetateYield 46%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

21.4 g (0.133 mol) of bromine are added to a stirred solution of 27.5 g (0.133 mol) of methyl 2-methylphenylglyoxylate O-methyloxime in 400 ml of tetrachloromethane. The mixture is then refluxed while irradiating with a 300 W Hg vapor lamp for four hours. It is then concentrated, the residue is taken up in ethyl acetate/water, and the organic phase is washed with H2O, dried with sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel with cyclohexane/ethyl acetate (9/1). 17.4 g (46%) of the abovementioned compound are obtained as an oil.

Workup

  1. temperatureThe mixture is then refluxed
  2. customwhile irradiating with a 300 W Hg vapor lamp for four hours
  3. concentrationIt is then concentrated
  4. washthe organic phase is washed with H2O
  5. dry with materialdried with sodium sulfate
  6. customevaporated
  7. customThe crude product is purified by chromatography on silica gel with cyclohexane/ethyl acetate (9/1)

Sources & evidence

ORD record
ord-4a0febc9d588446baa9a9744533a2ade
Source dataset
uspto-grants-1993_04
Patent number
US05206266

Reaction notes

Loading…