Triphenylphosphine → Methyl 5-bromo-2-(2-thienylmethoxy)benzoate

HRID 1455966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1455966
[Br:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:18][C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 694672-ThiophenemethanolHCID 77683Methyl 5-bromosalicylateHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 22105630Methyl 5-bromo-2-(2-thienylmethoxy)benzoateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl 5-bromosalicylate [prepared by treating methyl 5-bromosalicyclic acid with methanol and sulphuric acid] (4.62 g, 20 mmol) was dissolved in THF (150 mL) and treated with thiophene methanol (2.28 g, 20 mmol) and triphenyl phosphine (10.4 g, 40 mmol). The reaction was cooled in an ice bath and treated with DEAD (6.96 g, 20 mmol). The resultant orange solution was allowed to stir at ambient temperature under argon for 18 hours. The reaction mixture was evaporated and the residue subjected to chromatography (eluant: diethyl ether/hexane) to give methyl 5-bromo-2-(2-thienylmethoxy)benzoate as a pink oil (3.6 g, 55%).

Aufarbeitung

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe reaction mixture was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7aa99d7866d14afb8e8d97e262d8670f
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843942

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