1,2-Dibromoethane → 9-(2-bromoethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

HRID 1679822Notes

Reaction equation

HRID 1679822 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[Br:16][CH2:17][CH2:18]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][CH2:17][Br:16])[C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 6079846-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 8383119-(2-bromoethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

199 g. (1 mole) of 6-methyl-1,2,3,4-tetrahydro-carbazol-1-one and 376 g. (2 moles) of 1,2-dibromoethane are dissolved in 1000 ml. of toluene and stirred together with 1000 ml. of sodium hydroxide solution and 4.25 g. (12,5 m moles) of tetrabutylammoniumhydrogensulfate for 10 hours at 60° C. After evaporating the aqueous layer, distilling off the solvent and recrystallizing the residual crude product, 275 g. of 6-methyl-9-(2-bromoethyl)-1,2,3,4-tetrahydrocarbazol-1-one (90% of the theoretical) melting at 102° to 103° C. are obtained.

Workup

  1. customAfter evaporating the aqueous layer
  2. distillationdistilling off the solvent
  3. customrecrystallizing the residual crude product, 275 g

Sources & evidence

ORD record
ord-ad97838f529f400ba97cf80aacc53d3b
Source dataset
uspto-grants-1981_06
Patent number
US04271073

Reaction notes

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