1,4-Dibromobutane → 5-(4-Bromo-butoxy)-1-(4-fluoro-phenyl)-1H-indole

HRID 1633620Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:9]=[CH:10]2

Participants

Conditions

Temperature: 55 °C

Procedure

To 230 mg (1 mmol) 1-(4-Fluoro-phenyl)-1H-indol-5-ol in 4 ml acetone were added 280 mg (2 mmol) powdered K2CO3 and 0.24 ml (2 mmol) 1,4-dibromobutane. The suspension was stirred at 55° C. for 5 h, cooled to RT and concentrated. The crude product was extracted with water and ether, the combined organic phases were washed and dried with Na2SO4. Purification by column chromatography on silica gel with hexane/EtOAc 9:1 yielded 320 mg (88%) 5-(4-Bromo-butoxy)-1-(4-fluoro-phenyl)-1H-indole as light yellow solid, 59-61° C., MS: 361 (M, 1Br).

Workup

temperaturecooled to RT
concentrationconcentrated
extractionThe crude product was extracted with water and ether
washthe combined organic phases were washed
dry with materialdried with Na2SO4
customPurification by column chromatography on silica gel with hexane/EtOAc 9:1

Sources & evidence

ORD record: ord-bfe4c221a4dd4d6782a68a1a6a52ac90
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503907B2

Reaction notes

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