Water → 3-Fluoropropyl methanesulfonate

A solution of 3-fluoro-propan-1-ol (31.2 g, 400 mmol) in 300 mL of CH2Cl2 was treated with methanesulfonyl chloride (55 g, 38 mL, 480 mmol, 1.2 equiv) at 0° C. The resulting reaction mixture was gradually warmed to room temperature and stirred for 1-2 hours. When 1H NMR showed the reaction was complete, the reaction mixture was treated with H2O (100 mL), and the two layers were separated. The aqueous layer was extracted with CH2Cl2 (2×100 mL). The combined organic layers were washed with H2O (3×100 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the desired methanesulfonic acid 3-fluoro-propyl ester (57.2 g, 91% yield) as a yellow oil.

1. customThe resulting reaction mixture
2. customthe two layers were separated
3. extractionThe aqueous layer was extracted with CH2Cl2 (2×100 mL)
4. washThe combined organic layers were washed with H2O (3×100 mL)
5. dry with materialdried over MgSO4
6. customThe solvent was removed in vacuo

ORD record

ord-7950e57dd2d04a54956cc3e31cfa68c5

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895741B2