Reaktion #512242

Reaktionsgleichung

2-(4-(5-bromo-2-chlorobenzyl)phenyl)ethanol

allyl bromide

potassium hydroxide

→

2-(4-(2-(allyloxy)ethyl)benzyl)-4-bromo-1-chlorobenzene

Ausbeute 89.0%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with chloroform (3×1 mL)
2. 2
   Waschenwashed with brine (1 mL)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeEtOAc gave intermediate BI (246 mg, yield 89%)

Vorschrift

A mixture of 2-(4-(5-bromo-2-chlorobenzyl)phenyl)ethanol (intermediate BH) (245 mg, 0.75 mmol), allyl bromide (2.6 mL, 3.01 mmol), potassium hydroxide (84 mg, 1.5 mmol) and tetra-n-butylammonium iodide (13.9 mg, 0.037 mmol) was stirred at room temperature for 6 h. Water (1 mL) was added and extracted with chloroform (3×1 mL), washed with brine (1 mL) and dried (Na2SO4), filtered and evaporated. Preparative TLC using 10:1 hexane:EtOAc gave intermediate BI (246 mg, yield 89%). 1H NMR (300 MHz, CDCl3): δ 7.26-7.08 (m, 7H), 5.90 (m, 1H), 5.22 (m, 2H), 4.02 (s, 2H), 3.99 (m, 2H), 3.64 (t, J=6.9, 7.2 Hz, 2H), 2.89 (t, J=6.9, 7.2 Hz, 2H).

Quelle