Iodine → HCID 59656661, compound

HRID 2054912Notes

Reaction equation

HRID 2054912 reaction equation
[Li]CCCC.CCCCC.[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:13]=1[C:14]#[N:15].[I:24]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.O>[F:11][C:12]1[C:19]([I:24])=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[C:13]=1[C:14]#[N:15]

Participants

8

Reactant 5

HCID 807IodineHCID 8003PentaneHCID 24477Sodium ThiosulfateHCID 1456132-Fluoro-6-(trifluoromethyl)benzonitrileHCID 178418339Butyllithium

Product 1

HCID 59656661HCID 59656661, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2 M n-BuLi in pentane (1.62 mL, 3.24 mmol) in 8 mL of dry THF under N2 at −78° C. was added 2-fluoro-6-(trifluoromethyl)benzonitrile (612 mg, 3.24 mmol) in 2 mL of dry THF. The mixture was stirred at −78° C. for 30 min, followed by the addition of iodine (1070 mg, 4.22 mmol) in 2 mL of dry THF. The reaction mixture was warmed up and stirred for 2 h at room temperature. Water was added followed by a solution of Na2S2O3. The mixture was extracted with EtOAc. The organic layer was separated and washed with water and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography eluting with 5% EtOAc/hexane. The product fractions were collected and concentrated to afford 180 mg (17.7%) of 2-fluoro-3-iodo-6-trifluoromethylbenzonitrile as a brown dark solid.

Workup

  1. temperatureThe reaction mixture was warmed up
  2. stirringstirred for 2 h at room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 5% EtOAc/hexane
  11. customThe product fractions were collected
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b472a272c627460bbaad004ffdc5e480
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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