Methanol → 4-Bromo-2,6-dimethylbenzoic acid

A solution of 4-bromo-2,6-dimethyl-benzonitrile (8.0 g, 38 mmol), 5N NaOH (60 mL), and MeOH (60 mL) was stirred at 80° C. for 17 h. The reaction mixture was cooled to ambient temperature and the methanol evaporated. The resulting solution was extracted with dichloromethane (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated. GC-MS indicated that 70% of benzonitrile was converted to benzamide derivative. This material (7.0 g) was treated with 85% phosphoric acid (20 mL) and stirred at 150° C. for 18 h. After this time, the reaction mixture was cooled to ambient temperature and treated with water (30 mL). The resulting solution was extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated to afford 4-bromo-2,6-dimethyl-benzoic acid. The material was used without further purification.

1. customthe methanol evaporated
2. extractionThe resulting solution was extracted with dichloromethane (2×200 mL)
3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. additionThis material (7.0 g) was treated with 85% phosphoric acid (20 mL)
7. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
8. additiontreated with water (30 mL)
9. extractionThe resulting solution was extracted with ethyl acetate (2×200 mL)
10. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-f863e0942e934e4b888e5f89441f5586

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07968570B2