Hydrochloric Acid → 3-Chloro-5-(methylthio)benzonitrile

HRID 1015721

Reaktionsgleichung

Reaktionsgleichung von HRID 1015721
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[C:5]#[N:6].[CH3:11][S-:12].[Na+].C(N(CC)C(C)C)(C)C.Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Cl:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([S:12][CH3:11])[CH:9]=1)[C:5]#[N:6]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 4378561Sodium methanethiolateHCID 159658933-Bromo-5-chlorobenzonitrile

Produkt 1

HCID 668786863-Chloro-5-(methylthio)benzonitrileAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

(Step 1) A mixture of 3-bromo-5-chlorobenzonitrile (4.0 g), sodium methanethiolate (1.42 g), Pd2(dba)3 (84 mg), Xantphos (106 mg) and N,N-diisopropylethylamine (4.78 g) was stirred in toluene (100 ml) at 90° C. for 9 hr. The reaction mixture was treated with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to give 3-chloro-5-(methylsulfanyl)benzonitrile (2.6 g) as a solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Quellen und Nachweise

ORD-Eintrag
ord-61f2e09ff6c84555838fd9b8e48fb3a8
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985862B2

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