Title:
METHOD FOR PRODUCING ALKENYL HALIDE
Document Type and Number:
WIPO Patent Application WO/2017/033813
Kind Code:
A1
Abstract:
A method for producing an alkenyl halide represented by general formula (3) (wherein R represents a hydrogen atom or a methyl group; W represents a bivalent saturated hydrocarbon group having 2 to 10 carbon atoms; and X represents a chlorine atom, a bromine atom or a iodine atom), comprising reacting an alkenyl alcohol represented by formula (1) (wherein R and W are as defined above) with an halogenate thionyl represented by formula (2) (wherein X is as defined above) in a solvent in the presence of a base, said method being characterized in that the base is used in an amount of 0.001 to 0.3 mole relative to 1 mole of the alkenyl alcohol (1), the solvent is a hydrocarbon and/or a halogenated hydrocarbon, and the reaction temperature employed in the reaction is 60 to 140°C.
Inventors:
SATO JUNKO (JP)
UJITA KATSUJI (JP)
TSURUTA TAKUO (JP)
SUGIOKA TAKASHI (JP)
UJITA KATSUJI (JP)
TSURUTA TAKUO (JP)
SUGIOKA TAKASHI (JP)
Application Number:
PCT/JP2016/074028
Publication Date:
March 02, 2017
Filing Date:
August 17, 2016
Export Citation:
Assignee:
KURARAY CO (JP)
International Classes:
C07C17/16; C07C21/04; C07B61/00
Domestic Patent References:
| WO2011054885A1 | 2011-05-12 |
Foreign References:
| CN1483320A | 2004-03-24 | |||
| JPH0469350A | 1992-03-04 | |||
| US5384415A | 1995-01-24 | |||
| JPH11158092A | 1999-06-15 | |||
| JPS3110065B1 | ||||
| JPS4019321B1 | ||||
| JP2016094366A | 2016-05-26 | |||
| JP2016169192A | 2016-09-23 |
Other References:
MCINTOSH, JOHN M.: "Conformational stabilities of substituted azapropellanes: 2-methyl-1- azoniatricyclo[4.4.4.0 1,6] tetradecane salts", J. ORG. CHEM., vol. 47, no. 19, 1982, pages 3777 - 3779
KABALKA, G. W.: "A mild and convenient procedure for conversion of alkenes into alkyl iodides via reaction of iodine monochloride with organoboranes", J. ORG. CHEM., vol. 45, no. 18, 1980, pages 3578 - 3580, XP055372546
FRAZER, M. J. ET AL.: "Formation of alkyl bromides by thionyl bromide", CHEMISTRY AND INDUSTRY, 1954, pages 931 - 932
ZHANG, JUNJIE: "CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: a practical and convenient approach for the preparation of optically active chloroalkanes", TETRAHEDRON LETTERS, vol. 54, 2013, pages 2261 - 2263, XP028527042
ROBERTS, JOHN D.: "Small-ring compounds. IV. Interconversion reactions of cyclobutyl, cyclopropylcarbinyl, and allylcarbinyl derivatives", J. AM. CHEM. SOC., vol. 73, 1951, pages 2509 - 2520, XP002119993
TOI, HIROO: "Selective reduction of tertiary alkyl, benzyl, and allyl halides to hydrocarbons using lithium 9,9-di-n-butyl-9- borabicyclo[3.3.1]nonanate", TETRAHEDRON, vol. 37, 1981, pages 2261 - 2267, XP055372548
COX EUGENE F.: "Small-ring compounds. XXXIV. carbonium ion reactions of 1-methylcyclobutyl, (1-methylcyclopropyl)-carbinyl and (beta0methylallyl)-carbinyl derivatives", J. AM. CHEM. SOC., vol. 83, 1961, pages 2719 - 2724
GADWOOD, ROBERT C.: "Total synthesis of (±)- poitediol and (±)-dactylol", J. AM. CHEM. SOC., vol. 108, no. 20, 1986, pages 6343 - 6350, XP055372550
KABALKA, G. W.: "A mild and convenient procedure for conversion of alkenes into alkyl iodides via reaction of iodine monochloride with organoboranes", J. ORG. CHEM., vol. 45, no. 18, 1980, pages 3578 - 3580, XP055372546
FRAZER, M. J. ET AL.: "Formation of alkyl bromides by thionyl bromide", CHEMISTRY AND INDUSTRY, 1954, pages 931 - 932
ZHANG, JUNJIE: "CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: a practical and convenient approach for the preparation of optically active chloroalkanes", TETRAHEDRON LETTERS, vol. 54, 2013, pages 2261 - 2263, XP028527042
ROBERTS, JOHN D.: "Small-ring compounds. IV. Interconversion reactions of cyclobutyl, cyclopropylcarbinyl, and allylcarbinyl derivatives", J. AM. CHEM. SOC., vol. 73, 1951, pages 2509 - 2520, XP002119993
TOI, HIROO: "Selective reduction of tertiary alkyl, benzyl, and allyl halides to hydrocarbons using lithium 9,9-di-n-butyl-9- borabicyclo[3.3.1]nonanate", TETRAHEDRON, vol. 37, 1981, pages 2261 - 2267, XP055372548
COX EUGENE F.: "Small-ring compounds. XXXIV. carbonium ion reactions of 1-methylcyclobutyl, (1-methylcyclopropyl)-carbinyl and (beta0methylallyl)-carbinyl derivatives", J. AM. CHEM. SOC., vol. 83, 1961, pages 2719 - 2724
GADWOOD, ROBERT C.: "Total synthesis of (±)- poitediol and (±)-dactylol", J. AM. CHEM. SOC., vol. 108, no. 20, 1986, pages 6343 - 6350, XP055372550
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