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

HRID 1196981Notes

Reaction equation

HRID 1196981 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, while stirring, to 27.6 g (0.133 mol) of 2-methylphenylglyoxylic acid methyl ester O-methyl oxime dissolved in 400 ml of tetrachloromethane. Refluxing is then carried out for four hours with exposure to a 300 W Hg vapor lamp. Thereafter, the mixture is evaporated down, the residue is taken up in ethyl acetate/water and the solution is washed with water, dried with sodium sulfate and evaporated down. The crude product is purified by chromatography over silica gel using 9:1 cyclohexane/ethyl acetate. 17.4 g (46% of theory) of 2-bromomethylphenylglyoxylic acid methyl ester O-methyl oxime are obtained as an oil.

Workup

  1. temperatureRefluxing
  2. customThereafter, the mixture is evaporated down
  3. washthe solution is washed with water
  4. dry with materialdried with sodium sulfate
  5. customevaporated down
  6. customThe crude product is purified by chromatography over silica gel using 9:1 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-aa8ec6dcbab149728c314666383bbb61
Source dataset
uspto-grants-1992_05
Patent number
US05116866

Reaction notes

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