N-bromobutanimide → (11beta)-16-Bromo-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

HRID 2286324Notes

Reaction equation

HRID 2286324 reaction equation
[CH2:1]([S:3][C:4]1[C@:5]2([CH2:22][C@H:21]([OH:23])[C@@:20]3([F:24])[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:25])[CH:14]=4)[C@@H:7]2[CH2:8][CH:9]=1)[CH3:6])[CH3:2].[Br:26]N1C(=O)CCC1=O>ClCCl>[Br:26][C:9]1[CH2:8][C@H:7]2[C@H:10]3[C@:20]([F:24])([C@@H:21]([OH:23])[CH2:22][C@:5]2([CH3:6])[C:4]=1[S:3][CH2:1][CH3:2])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1291771217-Ethylthio-9-fluoro-11beta-hydroxyandrosta-1,4,16-triene-3-one

Product 1

HCID 70564041(11beta)-16-Bromo-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (11β)-17-(ethylthio)-9-fluoro-11-hydroxyandrosta-1,4,16-trien-3-one (181 mg) in dichloromethane (10 ml) containing N-bromosuccinimide (98 mg) is stirred at room temperature for 2 hours and the reaction mixture is subjected to preparative thin layer chromatography on silica gel plates to isolate the title compound.

Sources & evidence

ORD record
ord-27f3471f9fb74aaea34c7e92b9764f08
Source dataset
uspto-grants-1981_05
Patent number
US04265815

Reaction notes

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