Sodium Hydroxide → HCID 66764938, compound

Temperature

-78 °C

To a mixture of aluminum chloride (0.58 g, 4.34 mmol) and dichloromethane (23.2 mL) cooled to −78° C. was added 4-bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene (1.15 g, 3.94 mmol) in dichloromethane (6.00 mL) via a cannula to give a light yellow solution. The reaction mixture was allowed to warm to room temperature, stirred for 5 minutes, and then poured into an Erlenmeyer flask containing a cold 10% aqueous NaOH solution (75.0 mL). The mixture was extracted with dichloromethane (2×, 40.0 mL) and the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/hexanes to afford the desired product as a pale-yellow oil.

1. customto give a light yellow solution
2. temperatureto warm to room temperature
3. additionpoured into an Erlenmeyer flask
4. extractionThe mixture was extracted with dichloromethane (2×, 40.0 mL)
5. dry with materialthe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe crude residue was purified by silica gel chromatography
9. washeluting with 0-20% EtOAc/hexanes

ORD record

ord-656803c6232d4c6e8d949db47d899b43

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2