1-Bromo-3-chlorobenzene → 4-(3-Chlorophenyl)-2-methyl-3-butyn-2-ol

HRID 606790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606790
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1.[CH3:9][C:10]([OH:14])([C:12]#[CH:13])[CH3:11]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[Cl:8][C:4]1[CH:3]=[C:2]([C:13]#[C:12][C:10]([CH3:11])([OH:14])[CH3:9])[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 2

HCID 79281-Bromo-3-chlorobenzeneHCID 82582-Methyl-3-butyn-2-ol

Produkt 1

HCID 230063744-(3-Chlorophenyl)-2-methyl-3-butyn-2-olAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Add triethylamine (75 mL), 1-bromo-3-chlorobenzene (24.1 g, 0.126 mol), and 2-methylbut-3-yn-2-ol (15 mL, 0.152 mol) to a degassed mixture of bis(triphenylphosphine)palladium (II) dichloride (49 mg, 7.1 10−5 mol) and copper (I) iodide (2.4 mg, 1.26 10−5 mol). Stir at 90° C. for 72 h. Cool the reaction mixture to room temperature. Filter, concentrate and dissolve in ethyl acetate. Wash with water and dry the organic phase over sodium sulfate. Filter, concentrate and purify the residue by silica gel chromatography, eluting with hexane:ethyl acetate 6:1, to give the title compound (23 g, 94%).

Aufarbeitung

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationFilter
  3. concentrationconcentrate
  4. dissolutiondissolve in ethyl acetate
  5. washWash with water
  6. dry with materialdry the organic phase over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate
  9. custompurify the residue by silica gel chromatography
  10. washeluting with hexane:ethyl acetate 6:1

Quellen und Nachweise

ORD-Eintrag
ord-bf50737988824fb38228afe636909a32
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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