2-Nitropropane → 4-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)benzaldehyde

Temperature

0 °C

A solution of 3.5 g of 4-(heptafluoroisopropyl)-toluene (13.4 mmol) in 100 ml tetrachloromethane was heated to reflux. Then 2.63 g of N-bromosuccinimide (14.8 mmol) and 326 mg of dibenzoyl peroxide (1.34 mmol) were added in small portions. After 5 h the mixture was cooled to 0° C., filtered and the solvent was evaporated. The remaining residue was dissolved in 15 ml ethanol and was added to a suspension that had been prepared by addition of 2-nitropropane (1.4 ml, 15.5 mmol) to a solution of 340 mg sodium (14.8 mmol) in ethanol. This mixture was stirred for 3 days. Then it was filtered, the solvent was removed and the remaining residue was dissolved in EtOAc and washed with 1 N sodium hydroxide solution, 1 N HCl solution, saturated NaHCO3 solution and with brine. The EtOAc layer was then dried with magnesium sulfate, filtered and concentrated. Purification of the residue (silica gel; c-hexane/EtOAc 10:1) gave 1.1 g (30%) of 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzaldehyde as a light yellow oil. 1H-NMR (CDCl3, 300 MHz: δ 7.82 (d, J=8 Hz, 2H), 8.03 (d, J=8 Hz, 2H), 10.11 (s, 1H).

1. filtrationfiltered
2. customthe solvent was evaporated
3. dissolutionThe remaining residue was dissolved in 15 ml ethanol
4. additionwas added to a suspension that
5. filtrationThen it was filtered
6. customthe solvent was removed
7. dissolutionthe remaining residue was dissolved in EtOAc
8. washwashed with 1 N sodium hydroxide solution, 1 N HCl solution, saturated NaHCO3 solution and with brine
9. dry with materialThe EtOAc layer was then dried with magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customPurification of the residue (silica gel; c-hexane/EtOAc 10:1)

ORD record

ord-e6d81247fd784eafbacc72fb4e7e2380

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745477B2