2,4-Difluorophenyl isocyanate → HCID 10206258, compound

HRID 264048Notes

Reaction equation

HRID 264048 reaction equation
[CH2:1]([C:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:11]=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[N:38]=[C:39]=[O:40]>O1CCCC1.CCCCCC>[F:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[NH:38][C:39](=[O:40])[CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:11]=[N:10][N:9]=1

Participants

6

Reactant 3

HCID 5932582,4-Difluorophenyl isocyanateHCID 21469551HCID 21469551, compoundHCID 178418339Butyllithium

Product 1

HCID 10206258HCID 10206258, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

The compound from (a) above (1.5 g; 4.5 mmoles) was dissolved in tetrahydrofuran (20 mL), cooled to -20° C., and then treated dropwise with n-butyllithium (2.8 mL; 4.5 moles) for over 5 minutes. The solution was stirred for 5 minutes before adding 2,4-difluorophenyl isocyanate (0.7 g; 4.5 moles). The ice bath was removed and the solution gradually warmed to room temperature over 30 minutes, at which time the reaction was quenched with water (20 mL) and diluted with ethyl acetate. The layers were separated and the organic portion was washed with aqueous HCl (1N), aqueous sodium carbonate (10%), and brine. The solution was dried over magnesium sulfate, filtered, and stripped to dryness leaving a viscous liquid that was dissolved in 75% hexane/25% ethyl acetate and chromatographed using silica gel. Yield: 0.9 g (41%).

Workup

  1. customThe ice bath was removed
  2. temperaturethe solution gradually warmed to room temperature over 30 minutes, at which time the reaction
  3. customwas quenched with water (20 mL)
  4. additiondiluted with ethyl acetate
  5. customThe layers were separated
  6. washthe organic portion was washed with aqueous HCl (1N), aqueous sodium carbonate (10%), and brine
  7. dry with materialThe solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. customleaving a viscous liquid that
  10. customchromatographed

Sources & evidence

ORD record
ord-032dc72a8ba54c47b828301f2848f644
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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