Bromine → 6-Bromo-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276918Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].[Br:19]Br>ClCCCl>[Br:19][C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:18])[C:6]3([CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH2:17][CH2:16][CH2:15][C:13]=1[C:14]=23

Participants

Conditions

Temperature: -20 °C

Procedure

A 20 ml portion of 1,2-dichloroethane solution containing 0.50 g (1.62 mmol) of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]-indole-2(1H)-one was cooled to −20° C. and mixed with 0.10 ml (1.94 mmol) of bromine. The reaction solution was stirred at −20° C. for 1 hour, extracted with chloroform and then washed with saturated sodium thiosulfate aqueous solution and saturated sodium bicarbonate aqueous solution in that order. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained residue was re-precipitated from ethyl acetate-hexane to obtain 0.54 g of the title compound (86% in yield).

Workup

extractionextracted with chloroform
washwashed with saturated sodium thiosulfate aqueous solution and saturated sodium bicarbonate aqueous solution in that order
dry with materialAfter drying (Na2SO4)
customthe solvent was evaporated under a reduced pressure
customthe thus obtained residue was re-precipitated from ethyl acetate-hexane

Sources & evidence

ORD record: ord-179655c6e4854045b60b081636f77ad8
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355642B1

Reaction notes

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