1-Bromo-2-Chloroethane → 3,6-bis(2-chloroethoxy)-N-ethylcarbazole

HRID 268520Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18]C(=O)C)=[CH:12][CH:11]=3)(=O)[CH3:2].Br[CH2:25][CH2:26][Cl:27].C[O-].[Na+].[Cl:31]C1C=CC=CC=1>>[Cl:27][CH2:26][CH2:25][O:18][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:22][CH3:23])[C:8]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][C:5]([O:4][CH2:1][CH2:2][Cl:31])=[CH:6][CH:7]=3

Participants

Reactant 4

HCID 78491-Bromo-2-Chloroethane

HCID 7964Chlorobenzene

HCID 10942334Sodium Methoxide

HCID 12331788N-ethyl-3,6-carbazolediol diacetate

Product 1

HCID 215523293,6-bis(2-chloroethoxy)-N-ethylcarbazole

Procedure

To a stirred mixture of 31.3 g (0.1 mole) of N-ethyl-3,6-carbazolediol diacetate and 39.4 g (0.3 mole) of 1-bromo-2-chloroethane in 400 ml chlorobenzene is added 0.2 mole of sodium methoxide. Upon complete addition of the alkali, the mixture is refluxed with stirring for 18 hours, then cooled. The supernatant water layer is decanted and the residue is taken up in ethanol-chloroform to give 3,6-bis(2-chloroethoxy)-N-ethylcarbazole.

Workup

additionUpon complete addition of the alkali
temperaturethe mixture is refluxed
temperaturecooled
customThe supernatant water layer is decanted

Sources & evidence

ORD record: ord-65da1e8c3e0940259ac6214293fb65f4
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947593

Reaction notes

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