Sodium Carbonate → HCID 67187243, compound

HRID 735864Notes

Reaction equation

HRID 735864 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12162Benzonitrile, 4-bromo-HCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 67187243HCID 67187243, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of dibenzofuran-4-boronic acid (40 g, 0.19 mol), 4-bromobenzonitrile (34 g, 0.19 mol), sodium carbonate (120 g) in toluene (500 mL) and water (500 mL) was added tetrakis (triphenylphosphine)palladium (0) (11 g, 0.0095 mol) with stirring under N2 atmosphere. The reaction mixture was refluxed for 20 h. Toluene layer was separated, washed with water, dried and concentrated. The crude product was purified by column chromatography over silica gel (chloroform) to give the title compound (40 g, 79%).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. customToluene layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography over silica gel (chloroform)

Sources & evidence

ORD record
ord-4ad0ef4f46a7454ca2fa937269078967
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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