Dichloromethane → HCID 21914168, compound

HRID 434160Notes

Reaction equation

HRID 434160 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[Cl:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.ClCCl>COCCOC.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[Pd]Cl>[Cl:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[O:11][CH3:12])[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 788702-Bromo-4-nitroanisoleHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 21914168HCID 21914168, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10796Cesium carbonateSolvent

Procedure

To a flask containing a bi-phasic mixture of 2-bromo-4-nitroanisole (15.0 g, 64.6 mmol) and 3-chlorophenylboronic acid (12.1 g, 77.6 mmol) in ethylene glycol dimethyl ether (187.5 mL) and 2.0 N aqueous cesium carbonate (97 mL) was added 1-1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II), complex with dichloromethane (1:1) (1.5 g). The mixture was heated at reflux for 4 hours under a nitrogen atmosphere. The crude reaction mixture was partitioned between ethyl acetate (350 mL) and brine (250 mL) and then filtered through a Buchner funnel. Layers were separated and the organic layer was washed with brine (250 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to a dark oil. The crude residue was purified by flash chromatography on silica gel using dichloromethane as the eluent to afford 2-(3-chlorophenyl)-4-nitroanisole as a yellow solid (13.9 g, 59.4 mmol).

Workup

  1. additionTo a flask containing
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 4 hours under a nitrogen atmosphere
  4. customThe crude reaction mixture
  5. customwas partitioned between ethyl acetate (350 mL) and brine (250 mL)
  6. filtrationfiltered through a Buchner funnel
  7. customLayers were separated
  8. washthe organic layer was washed with brine (250 mL)
  9. dry with materialThe organic phase was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to a dark oil
  12. customThe crude residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-89af124e522740038733881a41d0db48
Source dataset
uspto-grants-2003_12
Patent number
US06670376B1

Reaction notes

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