3-Chlorobenzaldehyde → (4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

Temperature

-78 °C

To a solution of 3,4-dibromo-2,5-dichlorothiophene (2.00 g, 6.43 mmol) in THF (18 mL) at −78° C., was added n-BuLi (2.5M in hexane, 2.57 mL, 6.43 mmol) dropwise. After 30 min., 3-chlorobenzaldehyde (0.732 mL, 6.43 mmol) was added dropwise to the yellow solution. The resulting solution was stirred at −78° C. for 30 min. and allowed to warm to 0° C. After 30 min., the reaction was quenched by the addition of 25% aq. NH4OAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane) to afford the desired product as a pale yellow oil.

1. temperatureto warm to 0° C
2. waitAfter 30 min.
3. customthe reaction was quenched by the addition of 25% aq. NH4OAc
4. extractionThe aqueous layer was extracted with EtOAc
5. washthe combined organics were washed with water and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customThe crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane)

ORD record

ord-5ec3e8f4ff7345f4b17b6326447c023e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969394B2