4-(Trifluoromethyl)benzoyl chloride → 1-[4-(Trifluoromethyl)phenyl]pentan-1-one

Temperature

-78 °C

To a suspension of copper bromide-dimethylsulfide complex (11.0 g, 53.5 mmol) in 200 mL ether at −78° C. was added 65 mL of n-BuLi (1.6M, 104.0 mmol) dropwise. The mixture was stirred at −78° C. for 45 min, warmed to −40° C. for 10 min and then re-cooled to −78° C. A solution of 4-trifluoromethylbenzoyl chloride (10.0 g, 48.0 mmol) in 50 mL ether was added dropwise at −78° C. After addition was complete, the reaction was stirred at −78° C. for 30 min, quenched with saturated (sat.) ammonium chloride and allowed to warm to room temperature (RT). The mixture was poured into ether containing ca 10 mL methanol and was washed with a mixture of ammonium chloride/ammonium hydroxide. The combined aqueous layers were extracted with ether. The combined ether layers were dried (MgSO4), filtered and concentrated to give 11.0 g of a solid. 1H NMR (CDCl3) δ 8.05 (d,2H), 7.72 (d,2H), 2.99 (t,2H), 1.80-1.67 (m,2H), 1.50-1.35 (m,2H), 0.96 (t,3H). 19F NMR (CDCl3) δ −63.13.

1. temperaturewarmed to −40° C. for 10 min
2. temperaturere-cooled to −78° C
3. additionAfter addition
4. stirringthe reaction was stirred at −78° C. for 30 min
5. customquenched with saturated (sat.) ammonium chloride
6. temperatureto warm to room temperature (RT)
7. additionThe mixture was poured into ether containing ca 10 mL methanol
8. washwas washed with a mixture of ammonium chloride/ammonium hydroxide
9. extractionThe combined aqueous layers were extracted with ether
10. dry with materialThe combined ether layers were dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-554978147d054c718fb5a510c29450e4

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06818641B2