Dichloromethane → HCID 13576949, compound

HRID 544713Notes

Reaction equation

HRID 544713 reaction equation
[Br:1]Br.[CH3:3][CH:4]1[C:8]2[CH:9]=[CH:10][C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:12][C:7]=2[O:6][C:5]1=[O:19].C(Cl)Cl>C(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:12][C:7]2[O:6][C:5](=[O:19])[CH:4]([CH3:3])[C:8]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 135769393-Methyl-6-(morpholin-4-yl)-1-benzofuran-2(3H)-one

Product 1

HCID 13576949HCID 13576949, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 11 g (0.069 mole) of bromine in 50 ml of chloroform is added dropwise in the course of one hour, at from 0° to 5° C. while stirring, to a mixture of 15 g (0.064 mole) of 3-methyl-6-morpholinobenzofuran-2(3H)-one in 120 ml of chloroform. Subsequently the mixture is stirred at room temperature for 30 minutes. Methylene chloride is added to the reaction mixture, which is washed in succession with 10% strength sodium thiosulphate solution, dilute sodium bicarbonate solution and water. The crude product remaining after drying and concentrating by evaporation the organic phase is chromatographed over silica gel with petroleum ether/ether. Recrystallisation of the pure fractions from ether/petroleum ether yields 5-bromo-3-methyl-6-morpholinobenzofuran-2(3H)-one having a melting point of 99°-100° C.

Workup

  1. washis washed in succession with 10% strength sodium thiosulphate solution, dilute sodium bicarbonate solution and water
  2. customafter drying
  3. concentrationconcentrating by evaporation the organic phase
  4. customis chromatographed over silica gel with petroleum ether/ether
  5. customRecrystallisation of the pure fractions from ether/petroleum ether

Sources & evidence

ORD record
ord-d6d55121ef9046c28d9347ccb1edfc05
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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