Water → 3,4-Difluoro-1-(2-methoxyethoxy)benzene

To a solution of 3,4-difluoro-phenol (10 g, 76.9 mmol) (Aldrich) in N,N-dimethylformamide (100 mL) was added sodium hydride (4.6 g, 115 mmol) and 1-bromo-2-methoxy-ethane (12.8 g, 92.2 mmol) (Aldrich). The reaction mixture was stirred at room temperature for 2 h, then heated at 80 ° C. for 16 h. The reaction mixture was cooled to room temperature and poured into water, extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over dried over MgSO4, filtered and concentrated. The residue was purified with chromatography (EtOAc:Hexane=1:10) to give 1,2-difluoro-4-(2-methoxy-ethoxy)-benzene as colorless oil (Yield 6.3 g, 44%).

1. temperatureheated at 80 ° C. for 16 h
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionextracted with ethyl acetate
4. washwashed with water, brine
5. customdried
6. dry with materialover dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified with chromatography (EtOAc:Hexane=1:10)

ORD record

ord-c929d55c7fd64237a7e34378f1620719

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07495007B2