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Synlett 2011(14): 2025-2028  
DOI: 10.1055/s-0030-1261164
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Simple and Efficient One-Step Conversion of Benzonitrile into Methylarene under Mild Conditions

Étienne Ouellet, Donald Poirier*
Laboratory of Medicinal Chemistry, CHUQ (CHUL) - Research Center and Laval University, 2705 Laurier Blvd, Quebec, QC, G1V 4G2, Canada
Fax: +1(418)6542761; e-Mail: donald.poirier@crchul.ulaval.ca;
Further Information

Publication History

Received 16 June 2011
Publication Date:
10 August 2011 (online)

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Abstract

A very simple and efficient method has been developed for the synthesis of various methylarenes from the corresponding benzonitriles under mild conditions. The protocol uses Pearlman’s catalyst to achieve the transformation under an atmosphere of gaseous hydrogen and proceeds smoothly in many common solvents. A series of methylarenes were thus obtained in high yields and purities.

Key words

reduction - nitriles - palladium - methylarene - Pearlman’s catalyst

    References and Notes

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Typical Experimental Procedure for the Reduction of Benzonitrile to Methylarene
To a stirred solution of benzonitrile (0.15 mmol) in solvent (4 mL) was added Pd(OH)2/C [20 mol%, ≤50% wet, 20 mg (19 mol%) or 40 mg (38 mol%)]. The mixture was stirred at ambient temperature under 1 atm of hydrogen for 3-18 h. The catalyst was removed by filtration through a short pad of Celite and washed with EtOAc. The solvent was removed under reduced pressure to afford the reduced product.

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Optimized conditions use MeOH as solvent, 19 mol% of Pearlman’s catalyst [20% Pd(OH)2/C], 1 atm of gaseous H2 and 3 h of stirring at r.t. When the reaction was done on a larger scale, anhyd MeOH was used, and the organic layer was dried using MgSO4.