Phenetole → (7-Bromo-4-chloro-2-methyl-2,3-dihydrobenzofuran-5-yl)(4-ethoxyphenyl)methanone

To a suspension of compound 88 (2.4 g, 8.23 mmol) in CH2Cl2 (50 mL) were added oxalyl chloride (0.87 mL, 9.88 mmol) and catalytic amounts of DMF at room temperature. The mixture was stirred at room temperature for 2 hours. The mixture was evaporated in vacuo and dried under high vacuum. The crude acid chloride was dissolved with CH2Cl2 (45 mL) and cooled to 0° C. To the mixture was added phenetole (1.1 mL, 8.28 mmol) at 0° C. and stirred at 0° C. for 5 min. To the reaction mixture was added AlCl3 (1.1 g, 8.28 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 30 min, warmed up to room temperature and stirred at the temperature for 15 hours. The mixture was poured into ice-water and extracted with CH2Cl2 (50 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product 89 was carried on to the next step without further purification (3.15 g).

1. customThe mixture was evaporated in vacuo
2. customdried under high vacuum
3. dissolutionThe crude acid chloride was dissolved with CH2Cl2 (45 mL)
4. temperaturecooled to 0° C
5. stirringstirred at 0° C. for 5 min
6. stirringThe mixture was stirred at 0° C. for 30 min
7. temperaturewarmed up to room temperature
8. stirringstirred at the temperature for 15 hours
9. extractionextracted with CH2Cl2 (50 mL×2)
10. dry with materialThe combined organic layer was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe crude product 89 was carried on to the next step without further purification (3.15 g)

ORD record

ord-7b04bf45102b403c862356a8bd375ba5

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034921B2