Pyridine → Phenyl [2-fluoro-5-(trifluoromethyl)phenyl]carbamate

To a stirred solution of 2-fluoro-5-(trifluoromethyl)aniline (3.00 g, 16.7 mmol) in THF (80 mL) was added pyridine (2.71 mL, 33.5 mmol), followed by phenyl chloroformate (3.15 mL, 25.1 mmol) at rt. Some solid precipitated out. The mixture was stirred at rt overnight. Water was added to the reaction and it was extracted with EtOAc. The organic solution was washed with water (2×) and dried over MgSO4 and then filtered. The filtrate was concentrated in vacuo and purified by column chromatography (10:90 to 30:70 v/v EtOAc-hexanes) to afford the title compound (3.1 g, 62%). 1H-NMR (DMSO-d6) δ 10.36 (br s, 1H), 8.15 (d, J=7.1 Hz, 1H), 7.59 to 7.47 (m, 2H), 7.46 to 7.38 (m, 2H), 7.30 to 7.20 (m, 3H); TLC Rf=0.39 (9:1 v/v hexanes-EtOAc).

1. customSome solid precipitated out
2. additionWater was added to the reaction and it
3. extractionwas extracted with EtOAc
4. washThe organic solution was washed with water (2×)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. custompurified by column chromatography (10:90 to 30:70 v/v EtOAc-hexanes)

ORD record

ord-33b1d468d9f3417aa9cefbe9dfd27d48

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338595B2