Potassium Carbonate → 2-(3-Bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene

HRID 505519Notes

Reaction equation

HRID 505519 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Br:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN1C(=O)CCC1>[Br:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:20][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 185552,3-DichloronitrobenzeneHCID 25517Ammonium ChlorideHCID 226301803-Bromo-5-chlorophenol

Product 1

HCID 568336472-(3-Bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2,3-dichloronitrobenzene (764 mg, 3.99 mmol), 3-bromo-5-chlorophenol (1.65 g, 7.98 mmol) and potassium carbonate (661 mg, 4.79 mmol) were suspended in NMP (5 mL) and placed in an oil bath at 120° C. After 2 hours, the reaction was allowed to cool to room temperature, saturated aqueous ammonium chloride (10 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with dilute brine (4×50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by automated column chromatography on silica gel (80 g), eluting with 0-100% CH2Cl2/hexanes to yield the title compound. 1H NMR (CD3CN) δ 8.02 (dd, J=8.3 Hz, J=1.5 Hz, 1H), 7.88 (dd, J=8.2 Hz, J=1.6 Hz, 1H), 7.52 (dd, J=8.2 Hz, J=8.3 Hz, 1H), 7.38 (m, 1H), 7.07 (m, 1H), 6.97 (m, 1H).

Workup

  1. customplaced in an oil bath at 120° C
  2. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic fractions were washed with dilute brine (4×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by automated column chromatography on silica gel (80 g)
  8. washeluting with 0-100% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-87d3c660e6a54c859f4fba2caddc8efa
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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