2-Bromonaphthalene → 2-(4-Nitrophenylthio)naphthalene

HRID 2395331Notes

Reaction equation

HRID 2395331 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

Product 1

HCID 189716852-(4-Nitrophenylthio)naphthaleneYield 12%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

2-Bromonaphthalene (0.08 moles, 16.6 g), 4-nitrothiophenol (0.08 moles, 12,4 g), potassium carbonate (0.1 moles, 13.4 g), copper bronze (6.0 g) and cuprous chloride (0.02 moles, 2.0 g) were heated under reflux for 4 days in 300 ml pyridine. The solution was filtered hot, concentrated, dissolved in ethyl acetate and washed thoroughly with 2N HCl and water. The solution was dried over sodium sulfate, concentrated and purified by HPLC over silica gel eluted with 5% ethyl acetate in hexane. The product was recrystallized from ethyl acetate and hexane to yield 2-(4-nitrophenylthio)naphthalene 2.6 g, 12% in the first crop. Mass spec. (FD) 281.

Workup

  1. filtrationThe solution was filtered hot
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed thoroughly with 2N HCl and water
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by HPLC over silica gel
  8. washeluted with 5% ethyl acetate in hexane
  9. customThe product was recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-7fae9de9e87d408986b30100dba18b24
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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