Iodine → HCID 12786936, compound

HRID 725690Notes

Reaction equation

HRID 725690 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1)(=[O:3])[CH3:2].[I:11]I.C(O)(C)C.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[I-:11].[Br:10][C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH2:2][N+:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 807IodineHCID 1049PyridineHCID 3776IsopropanolHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 12786936HCID 12786936, compound

Procedure

To a stirred solution of 2-acetyl-6-bromopyridine (100 g; 0.5 mole) in 600 mL pyridine was added iodine (127 g; 0.5 mole). The mixture was heated on a steam bath for 45 minutes, and the product crystallized on cooling. The solid was filtered and the light yellow crystalline cake was rinsed twice with methylene chloride. After drying, 183 g (90%) was obtained. MP 176°-178° C.; silica gel TLC system: 95acetone: 5 isopropanol.

Workup

  1. temperatureThe mixture was heated on a steam bath for 45 minutes
  2. customthe product crystallized
  3. temperatureon cooling
  4. filtrationThe solid was filtered
  5. washthe light yellow crystalline cake was rinsed twice with methylene chloride
  6. customAfter drying
  7. custom183 g (90%) was obtained

Sources & evidence

ORD record
ord-fdae55a513b742c28bcefa581f5a4824
Source dataset
uspto-grants-1998_01
Patent number
US05707603

Reaction notes

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