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

HRID 728010Notes

Reaction equation

HRID 728010 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 27.5 g (0.133 mol) of 2-methylphenylglyoxylic acid methyl ester O-methyloxime dissolved in 400 ml of tetrachloromethane. The mixture is then refluxed for four hours while being exposed to a 300 W Hg vapor lamp, after which it 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 the abovementioned compound are obtained as an oil.

Workup

  1. temperatureThe mixture is then refluxed for four hours
  2. customafter which it 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

Sources & evidence

ORD record
ord-ad666c6874254fca87177d2fc14e971d
Source dataset
uspto-grants-1991_09
Patent number
US05047408

Reaction notes

Loading…