Reaktion #337446

Reaktionsgleichung

ethyl 2-mercaptoacetate

Sodium hydride

4-bromo-2-fluoro-benzaldehyde

→

title compound

Ausbeute 86.0%

6-bromo-benzo[b]thiophene-2-carboxylic acid ethyl ester

Ausbeute 86.0%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with hexanes (10 mL) twice
2. 2
   workup.STIRRINGThe reaction mixture is stirred for 15 minutes
3. 3
   Sonstigequenched with ice-water (100 g)
4. 4
   ExtraktionThe mixture is extracted with CH2Cl2 (50 mL×2)
5. 5
   TrocknenThe combined organic layers are dried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe crude product is purified via flash chromatography
9. 9
   Wascheneluting with 10% EtOAc/Hexanes
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

Sodium hydride (1.41 g, 35.32 mmol) is added to a round bottom flask and washed with hexanes (10 mL) twice. To the flask is added dimethyl sulfoxide (30 mL) and ethyl 2-mercaptoacetate (3.54 g, 29.43 mmol). The mixture is stirred for 10 minutes and 4-bromo-2-fluoro-benzaldehyde (4.78 g; 23.55 mmol) is added. The reaction mixture is stirred for 15 minutes and quenched with ice-water (100 g). The mixture is extracted with CH2Cl2 (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified via flash chromatography eluting with 10% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (5.75 g, 86%). 1H NMR (400 MHz, CDCl3): δ 8.00 (s, 1H), 7.99 (s, 1H), 7.75 (d, 1H), 7.48 (d, 1H), 4.38 (q, 2H), 1.39 (t, 3H).

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