2-Bromobenzaldehyde → 2-(1-Tridecynyl)benzaldehyde

HRID 255989

Reaktionsgleichung

Reaktionsgleichung von HRID 255989
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 2

HCID 811292-BromobenzaldehydeHCID 1177541-Tridecyne

Produkt 1

HCID 136885012-(1-Tridecynyl)benzaldehydeAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

Palladium acetate (96 mg) was added to a deaerated mixture of 2-bromobenzaldehyde (7.40 g, 40 mmol), 1-tridecyne (12.2 g, 68 mmol) and triphenylphosphine (320 mg) in dry triethylamine (160 ml) and the mixture was stirred at 105° C. under a nitrogen atmosphere overnight. After cooling, the precipitated triethylamine hydrobromide was filtered off and the filtrate was evaporated to a crude red oil. Chromatography on silica gel eluting with dichloromethane:petroleum ether [bp 60°-80° C.](1:1) afforded 7.12 g (63%) of the title compound of bp0.05 212° C. (Kugelrohr), M+ 284.2141 (C20H28O requires; 284.2140).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe precipitated triethylamine hydrobromide was filtered off
  3. customthe filtrate was evaporated to a crude red oil

Quellen und Nachweise

ORD-Eintrag
ord-a55ebc70d3c945ac88c73ed65d20afa2
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699995

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