3-Mercaptopropionic Acid → Poly(difluoromethylene), alpha-(2-((2-carboxyethyl)thio)ethyl)-omega-fluoro-

3-Mercaptopropanoic acid (3.2 g, 30.1 mmol) was dissolved in MeOH (20 mL) and stirred at RT. Powdered potassium hydroxide (3.72 g, 66.3 mmol) was added to the solution, followed by 3-bromo-1,1,1-trifluoropropane (6.14 g, 34.7 mmol). The solution was then stirred at 65° C. for 3 h and then it was quenched with 1N HCl until the pH of the solution was acidic. The mixture was extracted with DCM (3×30 mL), the combined organic phases were dried, concentrated and purified by silica gel chromatography (0-50% EtOAc/hexane) to give 3-((3,3,3-trifluoropropyl)thio)propanoic acid (5.5 g, 27.2 mmol, 90% yield) as colorless oil mixed with some white suspension: IR (Thin film) 2936, 1708 cm−1; 1H NMR (300 MHz, CDCl3) δ 2.86-2.78 (m, 2H), 2.78-2.58 (m, 4H), 2.52-2.25 (m, 2H); EIMS m/z 202.

1. stirringThe solution was then stirred at 65° C. for 3 h
2. customit was quenched with 1N HCl until the pH of the solution
3. extractionThe mixture was extracted with DCM (3×30 mL)
4. customthe combined organic phases were dried
5. concentrationconcentrated
6. custompurified by silica gel chromatography (0-50% EtOAc/hexane)

ORD record

ord-d858c3e5747143479581c1f84064853e

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937083B2