O-Xylene → 2-Cyano-4'-methylbiphenyl

HRID 369614Notes

Reaction equation

HRID 369614 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1([CH3:19])[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C(C)=CC=CC=1>O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[C:13]1[CH:14]=[CH:15][C:10]([CH3:19])=[CH:11][CH:12]=1)#[N:5]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 10340Sodium CarbonateHCID 133912-ChlorobenzonitrileHCID 79799Tolylboronic acid

Product 1

HCID 1455122-Cyano-4'-methylbiphenylYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

15 g of 2-chlorobenzonitrile, 14.8 g of p-tolueneboronic acid and 28.9 g of sodium carbonate in 40 ml of glycol and 10 ml of water were heated to 120° C. At 80° C., 0.1 mol % of Pd(O)(TPPTS)3. 9H2O dissolved in 3 ml of H2O was added. The reaction mixture was held at 120° C. for 12 hours. After cooling, 50 ml of xylene were added and the organic phase was separated off. Distillation gave 10.5 g of 2-cyano-4'-methylbiphenyl (b.p. 140° C./mbar).

Workup

  1. customAt 80° C.
  2. additionwas added
  3. temperatureAfter cooling
  4. customthe organic phase was separated off
  5. distillationDistillation

Sources & evidence

ORD record
ord-ad03934729884d139cfbf64f29d4c014
Source dataset
uspto-grants-2000_10
Patent number
US06140265

Reaction notes

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