Diethyl Ether → HCID 18687664, compound

To a solution of 1,2-difluoro-4,5-dimethoxybenzene (5 g, 28.71 mmol, Aldrich) in methylene chloride (300 mL) cooled to 0° C. was added aluminum chloride (14.16 g, 106.2 mmol, Fluka) in several portions. At the end of the addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 12 hours. Water was added to quench the reaction. Diethyl ether (200 mL) was added and the layers were separated. The aqueous layer was extracted with diethyl ether (50 mL). The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solids were filtered off and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, 60 Å silica gel, eluting with 10% ethyl acetate in hexanes) yielded 4,5-difluoro-2-methoxy-phenol as dark oil (3.75 g, 82%).

1. additionAt the end of the addition
2. customthe ice bath was removed
3. additionWater was added
4. customto quench
5. customthe reaction
6. customthe layers were separated
7. extractionThe aqueous layer was extracted with diethyl ether (50 mL)
8. washThe combined organic layers were washed with water, brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationThe solids were filtered off
11. concentrationthe filtrate was concentrated in vacuo
12. customPurification of the crude residue
13. washby flash chromatography (Biotage system, 60 Å silica gel, eluting with 10% ethyl acetate in hexanes)

ORD record

ord-21a571beb94745318e214520e781c68f

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07615634B2