Reaktion #313238

Reaktionsgleichung

2-(3-bromo-2-methyl-benzo[b]thiophen-7-yl)-propan-2-ol

Et3N

MsCl

→

title compound

Ausbeute 39.1%

3-Bromo-7-isopropenyl-2-methyl-benzo[b]thiophene

Ausbeute 39.1%

Lösungsmittel

CH2Cl2

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat RT
2. 2
   Sonstigeovernight
3. 3
   Waschenwashed with 0.1 M HCl (10 m), H2O (20 mL)
4. 4
   Trocknendried with Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification of the crude material by silica gel chromatography

Vorschrift

A solution of 2-(3-bromo-2-methyl-benzo[b]thiophen-7-yl)-propan-2-ol (0.98 g, 3.45 mmol) in CH2Cl2 910 mL) is treated with Et3N (0.72 mL, 5.18 mmol) and MsCl (0.29 mL, 3.80 mmol) at) 0° C. The reaction is stirred at 0° C. for 10 min, and at RT overnight. It is diluted with EtOAc (50 mL), washed with 0.1 M HCl (10 m), H2O (20 mL); dried with Na2SO4, filtered and concentrated. Purification of the crude material by silica gel chromatography gives the title compound (0.36 g, 1.35 mmol, 39%). 1H NMR (CDCl3): δ) 2.23 (s, 3H), 2.56 (s, 3H), 5.40 (s, 1H), 5.49 (s, 1H), 7.28 (s, 1H), 7.41 (t, J=7.1 Hz, 1H), 7.64 (d, J=7.9 Hz, 1H) ppm.

Quelle