Thiophenol → HCID 22287222, compound

HRID 841188Notes

Reaction equation

HRID 841188 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C[O-].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:8]=[C:7]([S:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 1856942-Fluoro-4-iodoanilineHCID 10942334Sodium Methoxide

Product 1

HCID 22287222HCID 22287222, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.578 g) was added to a deoxygenated mixture of 2-fluoro-4-iodoaniline (2.37 g), thiophenol (1.07 ml) and sodium methoxide (1.13 g) in ethanol (80 ml). The mixture was further deoxygenated by evacuation and refilling with argon (3 cycles) then heated under reflux with stirring under argon for 18 hours, cooled and filtered. The filter was washed with ether (3×20 ml) and the filtrates were combined and volatile material was removed by evaporation. The residue was treated with dichloromethane (50 ml), filtered and reconcentrated. This crude product was purified by chromatography on a silica gel Mega Bond Elut column eluting with 50-70% dichloromethane/hexane to give the title compound (1.851 g) as a solid. M.p. 48-49° C.; NMR: 5.5 (s, 2H), 6.8 (t, 1H), 7.0-7.1 (m, 5H), 7.25 (t, 2H).

Workup

  1. customThe mixture was further deoxygenated by evacuation and refilling with argon (3 cycles)
  2. temperaturethen heated
  3. temperatureunder reflux
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe filter was washed with ether (3×20 ml)
  7. customvolatile material was removed by evaporation
  8. additionThe residue was treated with dichloromethane (50 ml)
  9. filtrationfiltered
  10. customThis crude product was purified by chromatography on a silica gel Mega Bond Elut column
  11. washeluting with 50-70% dichloromethane/hexane

Sources & evidence

ORD record
ord-f320037870974127ac212032a5516450
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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