Hydrochloric Acid → HCID 43413487, compound

HRID 1022583Notes

Reaction equation

HRID 1022583 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=1.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][C:19]#N)=[CH:15][CH:14]=1.Cl.C([O:26]CC)C>II>[Cl:10][C:5]1[CH:4]=[C:3]([C:19](=[O:26])[CH2:18][O:17][C:16]2[CH:21]=[CH:22][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:8]=[CH:7][C:6]=1[Cl:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether4×HCID 290134-Bromo-1,2-dichlorobenzeneHCID 5794914-MethoxyphenoxyacetonitrileHCID 5462224Magnesium

Product 1

HCID 43413487HCID 43413487, compound

Reagents, catalysts & solvents 1

HCID 807IodineCatalyst

Conditions

Temperature
35 °C

Procedure

To a solution of magnesium (2.23 g) and iodine (5 mg) in diethyl ether (20 mL) was added dropwise a solution of 1-bromo-3,4-dichlorobenzene (20.7 g) in diethyl ether (20 ml), and the mixture was stirred at 35° C. for 1 hr. The reaction mixture was cooled to −10° C., and diethyl ether (100 mL) was added. A solution of (4-methoxyphenoxy)acetonitrile (10 g) in diethyl ether (20 ml) was added dropwise at −10° C., and the mixture was stirred for 1 hr while warming to room temperature. To the reaction mixture was added 1 N aqueous HCl solution (200 ml), and the mixture was stirred at room temperature for 1 hr, and extracted with ethyl acetate. The obtained extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (15.6 g).

Workup

  1. temperatureThe reaction mixture was cooled to −10° C.
  2. stirringthe mixture was stirred for 1 hr
  3. temperaturewhile warming to room temperature
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. extractionextracted with ethyl acetate
  6. extractionThe obtained extract
  7. washwas washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-33b59623f2c745a086f2513e3bdf40fb
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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