Potassium Carbonate → 1-Chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthalene

HRID 2295790Notes

Reaction equation

HRID 2295790 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([Cl:15])[C:13]=1Cl.[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([OH:30])=[CH:22][CH:21]=1>CN(C=O)C>[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([O:30][C:13]2[C:12]([Cl:15])=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[CH:9][C:8]=2[Cl:7])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117874-Chloro-1-naphtholHCID 883653,4,5-Trichloronitrobenzene

Product 1

HCID 132459461-Chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthaleneYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture containing 28.02 g (0.203 mole) of anhydrous potassium carbonate and 30.26 g (0.134 mole) of 3,4,5-trichloro-1-nitrobenzene in 300 ml dry DMF under an atmosphere of nitrogen and at room temperature was added 30.04 g (0.168 mole) of 4-chloro-1-naphthol. The flask was then placed in an oil bath which was heated. An internal reaction temperature of 105° C. was reached and maintained for 20 hours. After cooling the reaction mixture to room temperature most of the DMF was removed under vacuum. The residue was taken up in 1.5 L of 1:1 EtOAc to Et2O and 300 ml of H2O. The layers were separated and washed twice with 5% NaOH, twice with H2O, and finally once with a saturated aqueous NaCl solution. After drying over anhydrous Na2SO4 removal of the solvents afforded 48.73 g of a dark brown solid. This was recrystallized twice from hexane-ethyl acetate to afford 15.84 g of pale yellow needles; mp 121.5°-123° C. NMR (COCl3): δ6.18 (d, J=8 Hz, 1H), 7.25 (d, J=8 Hz 1H) 8.4-8.7 (m, 2H), 8.0-8.5 (m, 4H, contains 8.25 [S]).

Workup

  1. customThe flask was then placed in an oil bath
  2. temperaturewhich was heated
  3. customAn internal reaction temperature of 105° C.
  4. temperaturemaintained for 20 hours
  5. customwas removed under vacuum
  6. customThe layers were separated
  7. washwashed twice with 5% NaOH, twice with H2O
  8. dry with materialAfter drying over anhydrous Na2SO4 removal of the solvents

Sources & evidence

ORD record
ord-1fb72d10a9be48bb9b7f9e40775c161d
Source dataset
uspto-grants-1984_01
Patent number
US04426385

Reaction notes

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