Potassium Carbonate → 1-Bromo-2,5-dichloro-3-(2-chloro-6-nitrophenoxy)benzene

HRID 505546Notes

Reaction equation

HRID 505546 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][C:12]2[C:13]([N+:19]([O-:21])=[O:20])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:3]=1[Cl:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 185552,3-DichloronitrobenzeneHCID 684280893-Bromo-2,5-dichlorophenol

Product 1

HCID 684255121-Bromo-2,5-dichloro-3-(2-chloro-6-nitrophenoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3-bromo-2,5-dichlorophenol (8.0 g, 33 mmol) and 2,3-dichloronitrobenzene (6.4 g, 33 mmol) were dissolved in NMP (30 mL), followed by the addition of potassium carbonate (5.5 g, 40 mmol). The resulting suspension was placed in an oil bath at 120° C. for 7 hours, after which the reaction mixture was diluted with water (150 mL) and extracted with ethyl acetate (2×00 mL). The combined organic fractions were washed with water (3×100 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (330 g) eluting with 0-20% CH2Cl2/hexanes to afford the title compound. 1H NMR (CDCl3) δ 7.98 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.79 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.44 (dd, J=8.2 Hz, J=8.2 Hz, 1H), 7.40 (d, J=2.2 Hz, 1H), 6.54 (d, J=2.2 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×00 mL)
  2. washThe combined organic fractions were washed with water (3×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel (330 g)
  7. washeluting with 0-20% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-c7fe8dc214444911891a0cee29968636
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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