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

HRID 49495Notes

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-a02a88f0a9fe4a9c8b454315f934328f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706751B2

Reaction notes

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