3,4-Difluorobenzoyl chloride → 3,4-Difluorophenyl 2-[4-[2-(1-Pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl Ketone

A slurry of 3.23 g (10 mmol) of 2-[4-[2-(1-pyrrolidinyl)ethoxy)phenyl]benzo[b]thiophene in 50 mL of 1,2′dichloroethane was treated with 1.76 g (10 mmol) of 3,4-difluorobenzoyl chloride at 0° C. The mixture was protected from light and 4.4 mL (40 mmol) TiCl4 was added dropwise. The reaction was stirred at 0° C. for 5 h at which time it was quenched by carefully pouring it into 400 mL of saturated aqueous NaHCO3. To this was added EtOAc (200 mL), and the two layers were separated. The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo to give a crude oil which was purified by chromatography (SiO2; 2% MeOH in CHCl3) to afford 1.7 g (3.7 mmol; 37%) of the ketone as a viscous oil.

1. additionwas added dropwise
2. customwas quenched
3. additionby carefully pouring it into 400 mL of saturated aqueous NaHCO3
4. additionTo this was added EtOAc (200 mL)
5. customthe two layers were separated
6. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. customevaporated in vacuo
9. customto give a crude oil which
10. customwas purified by chromatography (SiO2; 2% MeOH in CHCl3)

ORD record

ord-874355640211463283c6df3784098cdc

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265575B1