Iodine → HCID 86663961, compound

HRID 712170Notes

Reaction equation

HRID 712170 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:5](N)=[C:4]([N+:15]([O-:17])=[O:16])[C:3]=1[F:18].[I:19]I>C(Cl)(Cl)Cl.S(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:3]([F:18])=[C:4]([N+:15]([O-:17])=[O:16])[C:5]([I:19])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:8]=1

Participants

5

Reactant 2

HCID 807IodineHCID 86654965HCID 86654965, compound

Product 1

HCID 86663961HCID 86663961, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 23665763Sodium BisulfiteSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cold solution of 4-bromo-3-fluoro-2-nitro-6-(pyridin-2-yl)aniline (4.0 g, 12.81 mmol) in chloroform (50 mL) was added iodine (18.21 g, 71.77 mmol) and the resulting mixture was stirred at 0° C. for 10 min followed by addition of isoamyl nitrile (3.44 mL, 25.63 mmol). The mixture was then heated up to 65° C. for 5 h. After completion of reaction (by TLC), the reaction was diluted with 10% sodium bisulfite and extracted with DCM (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel by using 20% EtOAc:hexane to obtain the desired product as an off white solid (2.0 g, 37%).

Workup

  1. temperatureThe mixture was then heated up to 65° C. for 5 h
  2. customAfter completion of reaction (by TLC)
  3. extractionextracted with DCM (3×100 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-6204dcc28a2c4edb806109aae4a68f06
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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