Water → (2-(4-Fluorophenoxy)-ethyl)-carbamic acid tert-butyl ester

Next, to a solution of 4-fluorophenol (0.47 g, 4.18 mmol) in DMF (10 mL) was added cesium carbonate (2.72 g, 8.36 mmol) at room temperature. The mixture was stirred at ambient temperature for 15 minutes, then methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester (1.00 g, 4.18 mmol) was added. The reaction mixture was stirred at 100° C. for 16 hours. Water was added and the mixture was concentrated in vacuo. Product mixture was dissolved in ethyl acetate and was washed with water, then with brine. The organic layer was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1), and obtained [2-(4-fluorophenoxy)ethyl]carbamic acid tert-butyl ester as yellow oil (0.61 g, 57.4% yield).

1. stirringThe reaction mixture was stirred at 100° C. for 16 hours
2. concentrationthe mixture was concentrated in vacuo
3. dissolutionProduct mixture was dissolved in ethyl acetate
4. washwas washed with water
5. dry with materialThe organic layer was dried over Na2SO4
6. customthe solvent was removed under reduced pressure
7. customThe residue was purified by column chromatography (ethyl acetate:hexane=7:1 to 4:1)

ORD record

ord-6ea6e05ed63f45a6a9ae7d06ee7857cb

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423175B2