Reaktion #619415

Reaktionsgleichung

Water

2-(2-bromo-4-fluoro-5-methylphenyl)propan-2-ol

(chloromethoxy)ethane

→

1-bromo-2-(2-(ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylbenzene

Ausbeute 89.0%

Lösungsmittel

DMF DIPEA

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with DCM (200 mL×2)
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel
7. 7
   Wascheneluted with PE-EA (30:1)

Vorschrift

To a solution of 2-(2-bromo-4-fluoro-5-methylphenyl)propan-2-ol (2.0 g, 8.1 mmol) in DMF:DIPEA (2:1, 9 mL) was added (chloromethoxy)ethane (1.53 g, 16.2 mmol). The reaction mixture was heated at 100° C. in microware equipment for 1.5 h. Water (200 mL) was added and the mixture was extracted with DCM (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (30:1) to give 1-bromo-2-(2-(ethoxymethoxy)propan-2-yl)-5-fluoro-4-methylbenzene (2.2 g, 89%) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.208-7.234 (m, 2H), 4.572 (s, 2H), 3.594 (q, J=7.0 Hz, 2H), 2.149 (s, 3H), 1.665 (s, 6H), 1.115 (t, J=7.0 Hz, 3H) ppm.

Quelle