Reaction #1552068

Reaction equation

1,1,1,3,3,3-hexafluoro-2-(2-(methyl(phenyl)amino)phenyl)propan-2-ol

→

desired compound

Yield 80.0%

10-methyl-9,9-bis(trifluoromethyl)-9,10-dihydroacridine

Yield 80.0%

Solvents

POCl3

Conditions

Workup

1. 1
   Temperaturethe solution refluxed under argon for 3 d
2. 2
   workup.DISTILLATIONExcess POCl3 was distilled off
3. 3
   workup.DISTILLATIONa short path distillation head
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CHCl3
5. 5
   workup.ADDITIONpoured into a 10% (v/v) aqueous ammoniacal solution
6. 6
   OtherThe organic layer was separated
7. 7
   Extractionthe aqueous layer extracted with Et2O (3×50 mL)
8. 8
   Washwashed with brine and water
9. 9
   Dryingdried over MgSO4
10. 10
    Otherthe solvent evaporated under reduced pressure
11. 11
    OtherThe residue was purified by flash column chromatography

Procedure

1,1,1,3,3,3-hexafluoro-2-(2-(methyl(phenyl)amino)phenyl)propan-2-ol (0.2 g, 0.57 mmol) was dissolved in 15 mL POCl3 and the solution refluxed under argon for 3 d. Excess POCl3 was distilled off using a short path distillation head, the residue was dissolved in CHCl3, poured into a 10% (v/v) aqueous ammoniacal solution and the biphasic system stirred at room temperature for one hour. The organic layer was separated and the aqueous layer extracted with Et2O (3×50 mL). The organic layers were combined, washed with brine and water and dried over MgSO4, and the solvent evaporated under reduced pressure. The residue was purified by flash column chromatography using 10% dichloromethane in hexanes as the eluent to yield 0.15 g (80%) of the desired compound as a light-blue oil. 1H NMR (400 MHz, CHCl3) δ 3.46 (s, 3H), 7.00 (m, 4H), 7.42 (m, 2H), 7.89 (m, 2H). 13C NMR (100 MHz, CHCl3) δ 29.8, 35.1, 111.8, 114.7, 120.3, 130.3 (quintet), 130.7, 141.8. 19F NMR (380 MHz, CHCl3) δ −65.9. HRMS (EI) calc for C16H11F6N [M]+ 332.0868, found 332.0874. IR (KBr plate) 479 (m), 693 (s), 709 (s), 758 (s), 848 (m), 954 (s), 1116 (s), 1163 (m), 1192 (s), 1260 (s), 1489 (s), 1573 (m), 1594 (m), 2840 (m), 2972 (m), 3054 (m) cm−1.

Source