4-Fluorothiophenol → 4-Bromo-1-{[(4-fluorophenyl)sulfanyl]methyl}-2-nitrobenzene

HRID 1988900Notes

Reaction equation

HRID 1988900 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N+:10]([O-:12])=[O:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 677894-FluorothiophenolHCID 81531DiisopropylethylamineHCID 127613784-Bromo-1-(bromomethyl)-2-nitrobenzene

Product 1

HCID 586564724-Bromo-1-{[(4-fluorophenyl)sulfanyl]methyl}-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-1-(bromomethyl)-2-nitrobenzene (0.60 g) in tetrahydrofuran (10 ml) was added 4-fluorothiophenol (1.2 ml) and diisopropylethylamine (0.45 ml). After stirring for 2 h the mixture was concentrated under vacuum and purified by column chromatography on silica, eluting with petroleum ether (40-60°):dichloromethane (9:1 to 8:1) to give the title compound (0.52 g).

Workup

  1. concentrationwas concentrated under vacuum
  2. custompurified by column chromatography on silica
  3. washeluting with petroleum ether (40-60°)

Sources & evidence

ORD record
ord-f40a363831074b65b40a55e21fce8045
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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