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Synlett
Volumn , Issue 11, 2008, Pages 1639-1642
Direct oxidative conversion of alkyl halides into nitriles with molecular iodine in aqueous ammonia
Author keywords

Ammonia; Halide; Iodine; Nitrile
Indexed keywords

ALKYL GROUP; AMMONIA; CARBON; HALIDE; IODINE; NITRILE;
EID: 48249149549     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078491     Document Type: Article
Times cited : (35)
References (41)
  • 4
    • 17144377599 scopus 로고    scopus 로고
    • Synthesis from Nitriles with Retention of the Cyano Group
    • Thieme: Stuttgart
    • (c) Murahashi, S.-I. Synthesis from Nitriles with Retention of the Cyano Group, In Science of Synthesis, Vol. 19; Thieme: Stuttgart, 2004, 345-402.
    • (2004) Science of Synthesis , vol.19 , pp. 345-402
    • Murahashi, S.-I.1
  • 5
    • 33747176696 scopus 로고    scopus 로고
    • Application of Nitriles as Reagents for Organic Synthesis with Loss of the Nitrile Functionality
    • Thieme: Stuttgart
    • (d) Collier, S. J.; Langer, P. Application of Nitriles as Reagents for Organic Synthesis with Loss of the Nitrile Functionality, In Science of Synthesis, Vol. 19; Thieme: Stuttgart, 2004, 403-425.
    • (2004) Science of Synthesis , vol.19 , pp. 403-425
    • Collier, S.J.1    Langer, P.2
  • 7
    • 0003543593 scopus 로고
    • Larock, R. C, Ed, VCH Publishers, Inc, New York
    • Comprehensive Organic Transformation; Larock, R. C., Ed.; VCH Publishers, Inc.: New York, 1989, 976-993.
    • (1989) Comprehensive Organic Transformation , pp. 976-993
  • 10
    • 2642654941 scopus 로고
    • Wiley: New York
    • (c) Cason, J. Org. Synth., Coll. Vol. III; Wiley: New York, 1955, 3.
    • (1955) Org. Synth., Coll , vol.3 , pp. 3
    • Cason, J.1
  • 40
    • 48249120676 scopus 로고    scopus 로고
    • Typical Procedure for Oxidative Conversion of Benzyl Halides into Nitriles with I2 To a mixture of 4-methylbenzyl chloride (140.6 mg, 1 mmol) and aq NH3 (3.0 mL, 45 mmol) was added I2 (533.0 mg, 2.1 mmol) at r.t. under an empty balloon. The obtained mixture was stirred at 60 °C. After 4 h at the same temperature, the reaction mixture was quenched with H2O (10 mL) and sat. aq Na2SO 3 (2 mL) at 0 °C and was extracted with Et2O (3×15 mL, The organic layer was washed with brine and dried over Na 2SO4 to provide p-tolunitrile in 82% yield in an almost pure state. If necessary, the product was purified by a column chromatography (SiO2; hexane-EtOAc, 4:1) to give pure p tolunitrile as a colorless solid; mp 25 °C. IR (NaCl, 2230 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.55 (2 H, d,J= 7.9 Hz, 7.27 2 H, d
    • 3): δ = 7.55 (2 H, d,J= 7.9 Hz), 7.27 (2 H, d, J = 7.9 Hz), 2.42 (3 H, s).
  • 41
    • 48249154464 scopus 로고    scopus 로고
    • Typical Procedure for Oxidative Conversion of Alkyl Halides into Nitriles with I2 A mixture of 3-phenylpropyl bromide (199.1 mg, 1 mmol) and aq NH3 (5.0 mL, 75 mmol) in a screw-capped glass vial (10 mL) was stirred at 60 °C for 24 h. Then, aq NH3 (3.0 mL, 45 mmol) and I2 (761.4 mg, 3.0 mmol) were added. After 4 h at the same temperature, the reaction mixture was quenched with H2O (10 mL) and sat. aq Na2SO3 (2 mL) at 0 °C and was extracted with Et2O (3 × 15 mL, The organic layer was washed with brine and dried over Na2SO4 to provide 3-phenylpropionitrile in 73% yield in an almost pure state. If necessary, the product was purified by column chromatography (SiO2; hexane-EtOAc, 4:1) to give pure 3-phenylpropionitrile as a colorless oil. IR (NaCl, 2250 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.34 2 H, t,J= 8
    • 2N: 198.1494; found: 198.1484.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.