Ethyl bromoacetate → [(7,7,8,8,8-Pentafluorooctyl)oxy]Acetic Acid

Temperature

20 °C

To a stirred solution of 6-(pentafluoroethyl)hexan-1-ol (500 mg) in tetrahydrofuran (10 ml) was added sodium hydride (60% dispersion in mineral oil; 118 mg) and the reaction was stirred at 20° C. for 30 mlnutes. Ethyl bromoacetate (379 mg) was added and the reaction was stirred for a further 3 hours. The reaction was quenched by the addition of ethanol (3 ml) followed by stirring for 30 mlnutes, then 2M sodium hydroxide (3 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid and then extracted with dichloromethane (3×100 ml). The combined organic layers were dried over magnesium sulphate and the solvent was removed in vacuo to give the title compound as a white solid (250 mg).

1. stirringthe reaction was stirred for a further 3 hours
2. customThe reaction was quenched by the addition of ethanol (3 ml)
3. stirringby stirring for 30 mlnutes
4. addition2M sodium hydroxide (3 ml) was added
5. stirringthe reaction was stirred for a further 2 hours
6. customThe reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml)
7. additionThe aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid
8. extractionextracted with dichloromethane (3×100 ml)
9. dry with materialThe combined organic layers were dried over magnesium sulphate
10. customthe solvent was removed in vacuo

ORD record

ord-d707a3df10714dff82ef28cebb2bcaf3

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07195752B2