4-Bromophenol → 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene

Temperature

120 °C

To a stirred solution of trifluoroethyl tosylate (1.5 g, 5.8 mmol) in DMF (20 mL) was added K2CO3 (4 g, 29.4 mmol) followed by p-bromo phenol (1.1 g, 6.46 mmol) at RT under an inert atmosphere. The reaction mixture was stirred at 120° C. for 6 h. The volatiles were evaporated under reduced pressure; the residue was diluted with water (5 mL) and extracted with EtOAc (3×30 mL). The organic layer was washed with water and brine, was dried over anhydrous Na2SO4, was filtered and was concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 5% EtOAc/hexane to afford the desired product (0.8 g, 3.13 mmol, 53.3%) as semi solid. 1H NMR (200 MHz, CDCl3): δ 7.44-7.38 (m, 2H), 6.86-6.80 (m, 2H), 4.38-4.25 (m, 2H).

1. customThe volatiles were evaporated under reduced pressure
2. additionthe residue was diluted with water (5 mL)
3. extractionextracted with EtOAc (3×30 mL)
4. washThe organic layer was washed with water and brine
5. dry with materialwas dried over anhydrous Na2SO4
6. filtrationwas filtered
7. concentrationwas concentrated in vacuo
8. customThe crude compound was purified by silica gel column chromatography
9. washeluting with 5% EtOAc/hexane

ORD record

ord-34a15f8c7dd440e4bc5fe99571e81366

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09414596B2