Water → benzofuran-2,3-dione 2-[O-(2-bromoethyl)-oxime] 3-(O-methyloxime)

HRID 2186678Notes

Reaction equation

HRID 2186678 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]1=[N:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+].[Br:21][CH2:22][CH2:23]Br.O>CN(C)C=O>[CH3:1][O:2][N:3]=[C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]1=[N:13][O:14][CH2:23][CH2:22][Br:21]

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 10340Sodium CarbonateHCID 178502623HCID 178502623, compound

Product 1

HCID 73782576benzofuran-2,3-dione 2-[O-(2-bromoethyl)-oxime] 3-(O-methyloxime)Yield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (0.0052 mol) of benzofuran-2,3-dione 3-(O-methyloxime) 2-oxime with 1.5 g (0.0141 mol) of sodium carbonate and 3 g (0.016 mol) of 1,2-dibromoethane in 5 ml of dimethylformamide are stirred at 80° C. for 6 hours. The reaction mixture is subsequently poured into water and extracted with diethyl ether. The organic phase is washed with aqueous potassium hydroxide solution and dried over sodium sulphate. The solvent is distilled off under reduced pressure, giving 1.1 g (70.7% of theory) of crude benzofuran-2,3-dione 2-[O-(2-bromoethyl)-oxime] 3-(O-methyloxime) as a mixture of stereoisomers which is reacted further without any purification.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase is washed with aqueous potassium hydroxide solution
  3. dry with materialdried over sodium sulphate
  4. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-7e4d97a86622499793133cbffb79603d
Source dataset
uspto-grants-2002_06
Patent number
US06407097B1

Reaction notes

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