p-Fluoronitrobenzene → 4-[2-[(4-Nitrophenyl)thio]ethyl]pyridine

HRID 515791Notes

Reaction equation

HRID 515791 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][SH:10])=[CH:4][CH:3]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([S:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 114466374-Pyridineethanethiol Hydrochloride

Product 1

HCID 7615184-[2-[(4-Nitrophenyl)thio]ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(pyridin-4-yl)ethanethiol hydrochloride (3.84 g, 21.8 mmol, 4-fluoro-1-nitrobenzene (6.12 g, 43.3 mmol), and K2CO3 (9.0 g, 65.1 mmol) in acetonitrile (150 mL) was refluxed overnight. The reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by column chromatography on silica gel (EtOAc/PE=1/1) to afford 2.0 g of 4-(2-((4-nitrophenyl)thio)ethyl)pyridine as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.55 (d, 2H), 8.14 (d, 2H), 7.34 (d, 2H), 7.15 (d, 2H), 3.30 (t, 2H), 3.01 (t, 2H).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue was purified by column chromatography on silica gel (EtOAc/PE=1/1)

Sources & evidence

ORD record
ord-f9665a8b65ec4c6cbec0b380a28c75f9
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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