Sodium Carbonate → 2-Cyano-4'-methylbiphenyl

HRID 274593Notes

Reaction equation

HRID 274593 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 162722-BromobenzonitrileHCID 79799Tolylboronic acid

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 77.7%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of o-bromobenzonitrile (40 g) and 4-methylbenzeneboronic acid (33 g) in DME (2 liters) was added tetrakis (triphenylphosphine) palladium (0) (7.58 g) and then sodium carbonate (1M, 592 ml). The mixture was stirred vigorously and heated at reflux for 18 hours. The solvent was removed in vacuo and the dark residue partitioned between ether (800 ml) and sodium carbonate (1M, 800 ml); the aqueous phase was extracted with ether (3×400 ml). The combined organic phases were dried and concentrated in vacuo to afford an orange oil which was crystallised from System C (1:3) using activated charcoal as a decolourising agent to afford a white solid (33.0 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe dark residue partitioned between ether (800 ml) and sodium carbonate (1M, 800 ml)
  5. extractionthe aqueous phase was extracted with ether (3×400 ml)
  6. customThe combined organic phases were dried
  7. concentrationconcentrated in vacuo
  8. customto afford an orange oil which
  9. customwas crystallised from System C (1:3)

Sources & evidence

ORD record
ord-64f958404f024c12bf6fe74e2add4133
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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