Hexylbenzene → 2-(4-Bromo-phenyl)-1-(4-hexyl-phenyl)-ethanone

To a 2 L three-necked flask, set up with a mechanical stirring, containing AlCl3 (85.661 g; 642.42 mmol) under N2, 4-hexylbenzene (IVb) (104.25 g; 642.42 mmnol) was added in one portion at room temperature. To this resulting orange suspension (4-bromo-phenyl)-acetyl chloride (IIIa) (125.000 g; 535.35 mmol) was added drop wise during 45 minutes without cooling. Then reaction mixture was stirred for 3 h until temperature cooled down to room temperature, time when no more foaming was observed. The deep brown mixture was then stirred at room temperature overnight. The black thick solution was poured under stirring into a mixture of ice and 1N HCl (800 mL), then the resulting white-orange solid was filtered, and washed successively with water, saturated solution of NaHCO3 and finally with water until pH of the filtrate was 7. The solid was washed with heptane (3×200 mL) and dried under vacuum at room temperature to give the title compound as a white powder (m=151.15 g) in a 79% yield. Melting point: 108° C.

1. customTo a 2 L three-necked flask, set up with a mechanical stirring
2. temperaturewithout cooling
3. customThen reaction mixture
4. stirringThe deep brown mixture was then stirred at room temperature overnight
5. additionThe black thick solution was poured
6. filtrationthe resulting white-orange solid was filtered
7. washwashed successively with water, saturated solution of NaHCO3 and finally with water until pH of the filtrate
8. washThe solid was washed with heptane (3×200 mL)
9. customdried under vacuum at room temperature

ORD record

ord-b3d630a4fc1e467aa048ffea32b857c4

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479575B2