Triphenylphosphine → 3-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

HRID 84426

Reaktionsgleichung

Reaktionsgleichung von HRID 84426
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][S:11][CH:12]=1)[C:5]#[N:6]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 753413-Bromo-4-hydroxybenzonitrileHCID 83731Thiophene-3-ethanolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 568341533-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-bromo-4-hydroxybenzonitrile (15.0 g) in THF (100 mL) was added 2-(3-thienyl)ethanol (7.94 mL) and triphenyl phosphine (19.84 g). The reaction was cooled to 0° C. and diethylazodicarboxylate (11.92 mL) was added dropwise. The reaction was stirred at room temperature for 16 h. The solvent was then reduced in vacuo and the residue redissolved in diethyl ether (100 mL). The mixture was stirred at 0° C. for 10 min and then filtered. The filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 3-bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile.

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for 10 min
  2. filtrationfiltered
  3. washThe filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified on silica

Quellen und Nachweise

ORD-Eintrag
ord-ca22d59813074d9f89ca12f80f9459cc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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