Water → HCID 86684907, compound

HRID 2402898Notes

Reaction equation

HRID 2402898 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.O.[OH-].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=1>ClCCl>[F:31][C:32]1[CH:37]=[CH:36][C:35]([S:38][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:34]([C:39]([F:42])([F:40])[F:41])[CH:33]=1

Participants

7

Reactant 5

HCID 962Water2×HCID 6422Trifluoroacetic acidHCID 6457TriphenylcarbinolHCID 14798Sodium HydroxideHCID 509980024-Fluoro-2-trifluoromethylbenzenethiol

Product 1

HCID 86684907HCID 86684907, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylmethanol (39.7 g, 149.4 mmol) was dissolved in the solution of crude 4-fluoro-2-trifluoromethyl-benzenethiol in dichloromethane (ca. 260 mL) of the preceding step and a solution of trifluoroacetic acid (21.2 g, 186 mmol) in dichloromethane (20 mL) was added at room temperature. After stirring for 15 h, the mixture was basified by subsequent addition of water (20 mL), concentrated aqueous sodium hydroxide solution (32% m/m, 26.9 g, 215 mmol) and water again (240 mL). Phases were separated, the aqueous layer was extracted with dichloromethane (100 mL) and the combined organic extracts concentrated in vacuo at 50° C. to a volume of ca. 330 mL. Ethanol (400 mL) was continuously added to the distillation, while the overall volume was kept constant (solvent exchange). The solution (ca. 300 mL) was allowed to cool to room temperature, crystallization started at 42° C. The suspension was stirred for 18 h at room temperature and for 1 h at 0° C. After filtration, the precipitate was washed with cold ethanol (100 mL) and dried in vacuo at 40° C. to give rise to the title compound as a white crystalline solid (52.5 g, 79%). MS (EI): m/z=243 [CPh3]+. 1H NMR (CDCl3, 600 MHz): δ 6.73 (ddd, J=2.8 Hz, 8.3 Hz, 8.3 Hz, 1H), 7.04 (dd, J=5.4 Hz, 8.8 Hz, 1H), 7.18-7.25 (m, 10H), 7.35-7.37 (m, 6H). Anal. Calcd for C26H18F4S: C, 71.22; H, 4.14; S, 7.31; F, 17.33. Found: C, 71.16; H, 4.26; S, 7.15; F, 17.09.

Workup

  1. customPhases were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (100 mL)
  3. concentrationthe combined organic extracts concentrated in vacuo at 50° C. to a volume of ca. 330 mL
  4. additionEthanol (400 mL) was continuously added to the distillation, while the overall volume
  5. customcrystallization
  6. customstarted at 42° C
  7. stirringThe suspension was stirred for 18 h at room temperature and for 1 h at 0° C
  8. filtrationAfter filtration
  9. washthe precipitate was washed with cold ethanol (100 mL)
  10. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-0067d1209b1b4e04aec21f12b6845b26
Source dataset
uspto-grants-2014_08
Patent number
US08796471B2

Reaction notes

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