Reaktion #2174208

Reaktionsgleichung

14

1,2,5-tris-(t-Butyldimethylsilyloxy)-3-chlorobenzene

NBS

→

4

Ausbeute 27.0%

5-Bromo-6-chloro-1,2,4-tris-(t-butyldimethylsilyloxy)benzene

Ausbeute 27.0%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times with diethyl ether (30 mL each)
2. 2
   Waschenthe combined extracts were washed with brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated
5. 5
   Sonstigecolumn chromatographed on silica gel using
6. 6
   workup.ADDITIONa mixture of hexane and diethyl ether (100:1) as eluent

Vorschrift

A solution of 0.100 g (0.20 mmol) of 14 and 0.0354 g (0.20 mmol) of NBS in 2 mL of DMF under argon was stirred at 50° C. for 2 day. The solution was diluted with 30 mL of water, extracted three times with diethyl ether (30 mL each), and the combined extracts were washed with brine, dried (MgSO4), concentrated, and column chromatographed on silica gel using a mixture of hexane and diethyl ether (100:1) as eluent to give 31.4 mg (27% yield) of 4 and 62.9 mg (54% yield) of 15. Compound 15: 1H NMR (CDCl3) δ 6.54 (s, 1H, Ar, C6-H), 1.03 (s, 18H, t-Bu), 0.97 (s, 9H, t-Bu), 0.23 (s, 12H, Me), 0.17 (s, 6H, Me).

Quelle