Boron tribromide → (4-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

HRID 490690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490690
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[C:14]([O:15]C)=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

Produkt 1

HCID 57431999(4-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (4-Methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (0.7 g, 2.8 mmol) in methylene chloride (18 mL) is added BBr3 (1.0 M, heptane, 8.6 mL, 8.6 mmol) at −20˜−30° C. The reaction mixture is allowed to warm to room temperature over 2 hrs, and TLC indicated clean conversion. The reaction is quenched by ice water, extracted with methylene chloride, dried over sodium sulfate, concentrated. Column chromatography on silica gel eluted with hexanes/ethyl acetate yields the title compound (0.4 g).

Aufarbeitung

  1. customThe reaction is quenched by ice water
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. washColumn chromatography on silica gel eluted with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-51a463cf10f7485c86739b63f923bbe9
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528160B2

Notizen zur Reaktion

Wird geladen…