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

HRID 1032372Notes

Reaction equation

HRID 1032372 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 over sodium sulfate and concentrated. 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 over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography on silica gel with cyclohexane/ethyl acetate (9/1)

Sources & evidence

ORD record
ord-050e80d3025942c4b308b94248385ea8
Source dataset
uspto-grants-1990_09
Patent number
US04957937

Reaction notes

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