Potassium Carbonate → HCID 86709940, compound

Temperature

20 °C

A mixture of 5-bromo-3-(tert-butyl)-2-hydroxybenzaldehyde (4.74 g, 18.42 mmol) and anhydrous potassium carbonate (2.83 g, 20.45 mmol) in anhydrous DMF (20.0 mL) was stirred under nitrogen in a water bath (20° C.) to give an orange-yellow suspension. After stirring for 20 min, 2-methoxyethoxymethyl chloride (2.40 mL, 21.19 mmol, technical grade) was added drop wise (20 min) to above suspension while maintaining an internal temperature of 20° C. The reaction mixture was stirred at room temperature for 3 h to give a canary yellow suspension. The reaction mixture was poured into ice-water (150 mL) and stirred at room temperature to give a yellow oily liquid, no solid formation was observed. After 30 min of stirring, the reaction mixture was extracted with dichloromethane (2×75 mL). The organic layer was removed, washed with water (1×50 mL) and dried over anhydrous magnesium sulfate, filtered and evaporated in-vacuo to give a pale yellow viscous liquid (6.7832 g). No purification was necessary and the crude product (purity >97%) was used directly in the next Step #3.

1. customto give an orange-yellow suspension
2. stirringAfter stirring for 20 min
3. temperaturewhile maintaining an internal temperature of 20° C
4. stirringThe reaction mixture was stirred at room temperature for 3 h
5. customto give a canary yellow suspension
6. stirringstirred at room temperature
7. customto give a yellow oily liquid
8. stirringAfter 30 min of stirring
9. extractionthe reaction mixture was extracted with dichloromethane (2×75 mL)
10. customThe organic layer was removed
11. washwashed with water (1×50 mL)
12. dry with materialdried over anhydrous magnesium sulfate
13. filtrationfiltered
14. customevaporated in-vacuo

ORD record

ord-43a66aeefbcc4257b1ffac18684dea89

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085606B2