Methanol → HCID 59180451, compound

Temperature

0 °C

To a cooled (0° C.) solution of commercially available 1-bromo-3-tert-butylbenzene (42.6 g; 199 mmol) in anhydrous dichloromethane (800 mL) was added chlorosulfonic acid (15.9 mL; 239.0 mmol) dropwise. After addition was complete, the reaction was stirred at 0° C. for an additional 30 minutes, allowed to gradually warm to room temperature and further stirred overnight. The reaction mixture was concentrated under reduced pressure to about 500 mL and washed with aqueous hydrochloric acid (20 mL; 20N). The organic layer was separated and dried over magnesium sulfate which resulted in formation of a white precipitate. Methanol (200 mL) was added to dissolve the precipitate. The organic solution was filtered and concentrated under reduced pressure to yield the title product as a white solid (53.0 g).

1. additionAfter addition
2. temperatureto gradually warm to room temperature
3. stirringfurther stirred overnight
4. concentrationThe reaction mixture was concentrated under reduced pressure to about 500 mL
5. washwashed with aqueous hydrochloric acid (20 mL; 20N)
6. customThe organic layer was separated
7. dry with materialdried over magnesium sulfate which
8. customresulted in formation of a white precipitate
9. dissolutionto dissolve the precipitate
10. filtrationThe organic solution was filtered
11. concentrationconcentrated under reduced pressure

ORD record

ord-ec15e6ef78154fbda7c8fb085807f063

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178699B2