Triphenylphosphine → 5-Bromo-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester

HRID 606371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606371
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[OH:10])=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19](O)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:11])=[CH:8][C:9]=1[O:10][CH:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[Cl:12])[CH3:20])=[O:4]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 260821-(2-Chlorophenyl)ethanolHCID 5462977Diethyl azodicarboxylateHCID 59857018Methyl 5-bromo-3-hydroxythiophene-2-carboxylate

Produkt 1

HCID 589704945-Bromo-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl esterAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Bromo-3-hydroxy-thiophene-2-carboxylic acid methyl ester (1.67 g, 7/04 mmol, 1.0 Eq.), 1-(2-Chloro-phenyl)-ethanol (1.43 g, 9.16 mmol, 1.3 Eq.) and triphenylphosphine (2.40 g, 9.16 mmol, 1.3 Eq.) were dissolved in anhydrous THF (30 mL) under nitrogen. The resultant solution was cooled to 0° C. and DEAD (1.4 mL, 9.16 mmol, 1.3 Eq.) was added dropwise. The reaction was warmed to ambient temperature and stirred for 4.5 hours. The crude reaction was purified by column chromatography (10% EtOAc/petroleum ether) to give the sub-title compound as a yellow solid (2.60 g, 6.92 mmol, 98%); 1H NMR (400 MHz, CDCl3) δ 1.68 (3H, d), 3.88 (3H, s), 5.71 (1H, q), 6.65 (1H, s), 7.23-7.33 (2H, m), 7.37 (1H, dd), 7.66 (1H, dd).

Aufarbeitung

  1. customThe crude reaction
  2. customwas purified by column chromatography (10% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-ae1a64cb8f9740f3a1ad39dec2f22877
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915305B2

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