Sodium Carbonate → HCID 18319281, compound

HRID 1701002Notes

Reaction equation

HRID 1701002 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)#[N:13].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]([C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[CH3:11])[CH:17]=[CH:16][CH:15]=1)#[N:13]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 18319281HCID 18319281, compoundYield 87.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 2-bromo-5-nitrotoluene (8.82 gm, 40.83 mmol) in 1,2-dimethoxyethane (150 mL) was added to a solution of tetrakis(triphenylphosphine)palladium(0) (2.35 gm, 2.04 mmol) in 1,2-dimethoxyethane (100 mL) under nitrogen at room temperature. A solution of 3-cyanophenylboronic acid (J. Med.Chem., 1997, 40, 4208)(9.0 gm, 61.25 mmol) in ethanol (45 mL) was added and stirred for 10 mins. Finally, 2M aqueous sodium carbonate (234 mL) was added and the mixture was heated under reflux for 18 h. After being cooled, the mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with water, dried (Na2SO4), concentrated under reduced pressure and triturated with diethyl ether to give 1-(3-cyanophenyl)-2-methyl-4-nitrobenzene (8.48 gm, 87%) as a brown solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 h
  3. temperatureAfter being cooled
  4. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-e6977849e2214d1bb11921f9821fb5f8
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

Loading…