Reaktion #58644

Reaktionsgleichung

3,4-bis(4-chlorophenyl)-2-methyl-2-butanol

3,4-Bis(4-chlorophenyl)-2-methyl-2-butanol

chloroacetonitrile

sulfuric acid

→

title compound

N-[2,3-Bis(4-chlorophenyl)-1,1-dimethylpropyl]chloroacetamide

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction mixture was poured onto ice (20 g)
2. 2
   Extraktionthe product was extracted with EtOAc (3×20 mL)
3. 3
   WaschenThe combined extracts were washed with brine/saturated aqueous sodium bicarbonate
4. 4
   Trocknendried over anhydrous MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to dryness

Vorschrift

To a solution of 3,4-bis(4-chlorophenyl)-2-methyl-2-butanol (Step B, 1.4 g, 4.5 mmol) and chloroacetonitrile (0.57 mL, 9.1 mmol) in acetic acid (0.7 mL) at −10° C. was added concentrated sulfuric acid (0.31 mL, 14 mmol). After stirring at −10° C. for 15 min and room temperature for 2 h, the reaction mixture was poured onto ice (20 g), and the product was extracted with EtOAc (3×20 mL). The combined extracts were washed with brine/saturated aqueous sodium bicarbonate, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.19 (ABq, 4H), 7.06 (d, 2H), 6.95 (d, 2H), 3.93 (ABq, 2H), 3.89 (dd, 1H), 3.10 (dd, 1H), 2.99(dd, 1H), 1.43 (s, 3H), 1.25 (s, 3H). LC-MS: m/e 384 (M+H)+ (3.9 min).

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