Diethyl Ether → Tert-butyl 4-(trifluoromethoxy)phenylcarbamate

A solution of 4-(trifluoromethoxy)phenyl isocyanate (9.75 g, 48.0 mMol) in THF (100 mL) was cooled to 0° C., and a 1.0 M THF solution of potassium tert-butoxide (53 mL, 53 mMol) was added dropwise. The mixture was allowed to warm to room temperature, and stirred for 7 hours. The solution was poured into a mixture of saturated ammonium chloride solution (200 mL), and diethyl ether (200 mL). Enough water was added to redissolve the ammonium chloride that had crashed out, the mixture was shaken in a separatory funnel, and the layers were separated. The organic phase was washed with saturated ammonium chloride (100 mL), water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated in-vacuo. The residue was purified over silica gel, eluting with 10%-20% ethyl acetate/heptane to yield 11.7 g of white solids as product. NMR (500 MHz, DMSO) δ 9.54 (s, 1H), 7.54 (d, 2H, J=7 Hz), 7.23 (d, 2H, J=8 Hz), 1.45 (s, 9H). Yield=88%.

1. stirringthe mixture was shaken in a separatory funnel
2. customthe layers were separated
3. washThe organic phase was washed with saturated ammonium chloride (100 mL), water (100 mL), brine (100 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in-vacuo
6. customThe residue was purified over silica gel
7. washeluting with 10%-20% ethyl acetate/heptane

ORDレコード

ord-e168cb9ce68c4183ac49619b469decf8

出典データセット

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07829571B2