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 MsCl (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-239d50fc6b1f42d98fc2668d81cb4d54

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129259B2