1,4-Dibromobutane → 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

HRID 2212529Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:27][CH2:28][CH2:29][CH2:30][CH2:31]Br>CC(C)=O.CCOCC.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH2:31][CH2:30][CH2:29][CH2:28][Br:27])=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

290 mg (1 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester in 5 ml acetone were treated with 320 mg (3 mmol) K2CO3 (powdered) and 0.23 ml (2 mmol) 1,4-dibromobutane. The suspension was stirred at 50° C. for 4 h, cooled to RT, and was diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 210 mg (49%) 5-(4-Bromo-butoxy)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as colorless solid, MS: 423 (M, 1Br, 1Cl).

Workup

temperaturecooled to RT
extractionThe aqueous phase was extracted with ether
washthe organic phases were washed with water
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-7f17dae9edb746adbb3d4420bb4c9338
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07102007B2

Reaction notes

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