1-Bromonaphthalene → 1-(4-Nitrophenylthio)naphthalene

HRID 55077

Reaction equation

HRID 55077 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][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[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 3

HCID 70011-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

Product 1

HCID 189716701-(4-Nitrophenylthio)naphthaleneYield 35.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Procedure

1-Bromonaphthalene (0.15 mole, 31.0 g),4-nitrothiophenol 0.11 mole, 17.0 g), potassium carbonate (0.15 moles, 20.7 g), copper bronze (0.3 moles, 18.9 g) and cuprous chloride (0.06 moles, 6.0 g) were refluxed in 500 ml pyridine for 3 days. The reaction was filtered while hot, and then concentrated. Ethyl acetate was added and the solution washed with water and 5N HCl, dried over sodium sulfate and concentrated. The product was purified twice by HPLC over silica gel eluted with 20% ethyl acetate/hexane followed by 5 ethyl acetate/hexane to yield 1-(4-nitrophenylthio)naphthalene 11.0 g, 26%. Mass Spec (FD) 282. Calculated for C16H11NO2S: C, 68.31 H, 3.94, N, 4.98. Found: C, 68.52; H, 4.00; N, 4.77.

Workup

  1. filtrationThe reaction was filtered while hot, and
  2. concentrationthen concentrated
  3. additionEthyl acetate was added
  4. washthe solution washed with water and 5N HCl
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified twice by HPLC over silica gel
  8. washeluted with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6d866d63b9524845b6be5c08298412a8
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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