Hydrochloric Acid → HCID 23028604, compound

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.701 ml, 1.10 mmol) was added to a tetrahydrofuran (5 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (303 mg, 1.00 mmol) obtained in Example 5. The temperature of the resulting mixture was raised to room temperature and then stirred for 10 minutes. After cooling the reaction mixture to −78° C., benzoyl chloride (0.140 ml, 1.20 mmol) was added thereto dropwise. The reaction mixture was stirred at −78° C. for 30 minutes. The temperature of the mixture was then raised to OC over 3 hours. After addition of 1N hydrochloric acid (2.0 ml), the mixture was extracted with ethyl acetate. The extracts were combined, washed successively with water, a saturated aqueous solution of sodium bicarbonate, and brine, dried over MgSO4, and then concentrated. The residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane). The solid thus obtained was washed with hexane, whereby the title compound (200 mg, 49%) was obtained as a colorless solid.

1. temperatureAfter cooling the reaction mixture to −78° C.
2. stirringThe reaction mixture was stirred at −78° C. for 30 minutes
3. temperatureThe temperature of the mixture was then raised to OC over 3 hours
4. extractionthe mixture was extracted with ethyl acetate
5. washwashed successively with water
6. dry with materiala saturated aqueous solution of sodium bicarbonate, and brine, dried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane)
9. customThe solid thus obtained
10. washwas washed with hexane, whereby the title compound (200 mg, 49%)
11. customwas obtained as a colorless solid

ORD record

ord-26853abf268846089f196559208b4c56

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2