Sodium Carbonate → 3-(4-bromophenyl)benzonitrile

HRID 858580Notes

Reaction equation

HRID 858580 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(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>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 13938513-(4-bromophenyl)benzonitrileYield 39.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a magnetically stirring solution of 3-cyanophenyl boronic acid (0.62 g, 4.24 mmol) and 1-bromo-4-iodobenzene (1.0 g, 3.53 mmol) in anhydrous DMF (7.0 mL), under argon at room temperature, was added 2M sodium carbonate solution (7.0 mL) followed by Pd(PPh3)4 (0.21 g, 0.18 mmol). The resulting mixture was heated to 75° C. overnight. The resulting dark reaction mixture was cooled to room temperature filtered to remove the solids and the resultant filtrate was poured into water (50 mL) and extracted with EtOAc (2×25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (5% EtOAc in Hexanes) to yield the intermediate bromide as a white solid (0.36 g, 33%).

Workup

  1. customThe resulting dark reaction mixture
  2. temperaturewas cooled to room temperature
  3. filtrationfiltered
  4. customto remove the solids
  5. additionthe resultant filtrate was poured into water (50 mL)
  6. extractionextracted with EtOAc (2×25 mL)
  7. washThe organics were washed with water (50 mL) and brine (50 mL)
  8. dry with materialthen dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified by flash chromatography (5% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-d8598b58fe614d1f88edbdb94a781154
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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