Boron tribromide → Methyl 5-hydroxybenzo[b]thiophene-2-carboxylate

HRID 493178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493178
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([O:14]C)=[CH:13][C:7]=2[CH:6]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 23261726Methyl 5-methoxybenzo[b]thiophene-2-carboxylate

Produkt 1

HCID 13662999Methyl 5-hydroxybenzo[b]thiophene-2-carboxylateAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The above prepared 5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (0.199 g, 0.895 mmol) was dissolved in 6 mL of CH2Cl2, cooled to 0° C., and treated with BBr3 (1.79 mL of 1M solution in CH2Cl2, 2 eq.). After 2 additional h at 0° C., the reaction mixture was carefully poured onto crashed ice, twofold extracted with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=7/3) yielded 0.145 g of the title compound as off-white solid.

Aufarbeitung

  1. additionAfter 2 additional h at 0° C., the reaction mixture was carefully poured
  2. extractiontwofold extracted with AcOEt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3d30292e24f04efa8fb228637cb91172
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534788B2

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