Hexane → 4-(4-Chlorobenzoyl) 3,5-dichlorotoluene

A stirred, -60° C. solution of 3,5-dichlorotoluene (805 mg, 5.00 mmol) in tetrahydrofuran (5 mL) under nitrogen atmosphere was treated dropwise over 10 minutes with a 1.6M solution of n-butyllithium in hexane (3.3 mL, 5.25 mmol). After addition was complete residual n-butyllithium in the addition funnel was rinsed into the reaction mixture with tetrahydrofuran (1 mL). The reaction mixture was stirred 30 minutes at -55° and then a solution of p-chlorobenzoylchloride (875 mg, 5.00 mmol) in tetrahydrofuran (1.0 mL) was added dropwise over 15 minutes. The mixture was kept at -55° to -30° C. for 2 hours, stirred 2 hours at ambient temperature, and quenched by addition of saturated aqueous ammonium chloride (1.1 mL). After stirring 15 minutes, sodium sulfate (1.1 g) was added, and the mixture was stirred an additional 15 minutes. The solution was decanted, the solids were washed with diethyl ether, and the combined solution and wash were evaporated under reduced pressure. The residue was recrystallized from ethanol (15 mL) to provide 0.78 g (52%) 4-(4-chlorobenzoyl)-3,5-dichlorotoluene.

1. additionAfter addition
2. washwas rinsed into the reaction mixture with tetrahydrofuran (1 mL)
3. waitThe mixture was kept at -55° to -30° C. for 2 hours
4. stirringstirred 2 hours at ambient temperature
5. customquenched by addition of saturated aqueous ammonium chloride (1.1 mL)
6. stirringAfter stirring 15 minutes
7. additionsodium sulfate (1.1 g) was added
8. stirringthe mixture was stirred an additional 15 minutes
9. customThe solution was decanted
10. washthe solids were washed with diethyl ether
11. washthe combined solution and wash
12. customwere evaporated under reduced pressure
13. customThe residue was recrystallized from ethanol (15 mL)

ORD record

ord-5665a5adbd134bca9d7a499d101c4da9

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04590201