Anisole → HCID 65639687, compound

To a solution of acid 8 (10 g, 45.2 mmol) in CH2Cl2 (200 mL) were added oxalyl chloride (4.8 mL, 54.3 mmol) and catalytic amounts of DMF at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was concentrated in vacuo and dried under high vacuum. The crude acid chloride was dissolved with CH2Cl2 (200 mL) and cooled to 0° C. To the mixture was added anisole (5.0 mL, 45.2 mmol) at 0° C. and stirred at 0° C. for 5 min. To the reaction mixture was added AlCl3 (6.0 g, 45.2 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 2 hours, warmed up to room temperature and stirred at room temperature for 15 hours. The mixture was poured into ice-water and extracted with CH2Cl2 (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was tritulated with MeOH (100 mL) and stirred at 0° C. for 1 hour. The precipitated solid was filtered and washed with MeOH (50 mL). The solid was dried under high vacuum and used without further purification (11.7 g, 83%).

1. concentrationThe mixture was concentrated in vacuo
2. customdried under high vacuum
3. dissolutionThe crude acid chloride was dissolved with CH2Cl2 (200 mL)
4. temperaturecooled to 0° C
5. stirringstirred at 0° C. for 5 min
6. stirringThe mixture was stirred at 0° C. for 2 hours
7. temperaturewarmed up to room temperature
8. stirringstirred at room temperature for 15 hours
9. extractionextracted with CH2Cl2 (100 mL×2)
10. dry with materialThe combined organic layer was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. stirringstirred at 0° C. for 1 hour
14. filtrationThe precipitated solid was filtered
15. washwashed with MeOH (50 mL)
16. customThe solid was dried under high vacuum
17. customused without further purification (11.7 g, 83%)

ORD record

ord-6a3233a28f26482ebf3e02ad47a1bdf6

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006187B2