Dichloromethane → 6-Methoxy-2-[4-(methylsulfanyl)phenyl]-1-(4-nitrophenoxy)naphthalene

HRID 748917Notes

Reaction equation

HRID 748917 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[C:8]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2.F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.ClCCl>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[C:8]([C:14]1[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9590p-FluoronitrobenzeneHCID 685188176-Methoxy-2-[4-(methylsulfanyl)phenyl]naphthalen-1-ol

Product 1

HCID 685159406-Methoxy-2-[4-(methylsulfanyl)phenyl]-1-(4-nitrophenoxy)naphthaleneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a solution of 6-methoxy-2-(4-methylsulfanyl-phenyl)-naphthalen-1-ol (1.98 g, 6.68 mmol), 4-fluoro-nitrobenzene (0.78 mL, 7.34 mmol) and phosphazene base P4-t-butyl (6.7 mL of 1M in hexane, 6.7 mmol) in N,N-dimethylformamide (30 mL) at ambient temperature for 4 hours. Dilute the reaction with dichloromethane, wash with 1N aqueous hydrochloric acid, water, dry with solid magnesium sulfate and chromatograph on silica gel with hexane/ethyl acetate mixtures to give 2.18 g of 6-methoxy-2-(4-methylsulfanyl-phenyl)-1-(4-nitro-phenoxy)-naphthalene (78%)

Workup

  1. additionDilute
  2. washwash with 1N aqueous hydrochloric acid, water
  3. dry with materialdry with solid magnesium sulfate and chromatograph on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-d2f7f73d132b4449aec46074f0e0b646
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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