2-Hydroxybenzonitrile → 2-Hydroxy-5-iodo-benzonitrile

HRID 920282Notes

Reaction equation

HRID 920282 reaction equation
C(S(O)(=O)=O)(F)(F)F.[OH:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C1C(=O)N([I:25])C(=O)C1>CC#N>[OH:9][C:10]1[CH:17]=[CH:16][C:15]([I:25])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 119072-HydroxybenzonitrileHCID 62406Trifluoromethanesulfonic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 70230402-Hydroxy-5-iodo-benzonitrileYield 81,626.898%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

CF3SO3H (40 mL) was added dropwise to a solution of 2-hydroxy-benzonitrile (47.6 g, 0.400 mmol) in CH3CN (500 mL) at 0° C., and then stirred at 0° C. for 20 min, then NIS (108 g, 0.48 mmol) was added. The reaction mixture was stirred at rt overnight, concentrated, then diluted with H2O (300 mL) and extracted with EA (300 mL×3). The combined organic parts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification via FC (PE/EtOAc=5/1) afforded the title compound as a white solid (80 g).

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. concentrationconcentrated
  3. additiondiluted with H2O (300 mL)
  4. extractionextracted with EA (300 mL×3)
  5. dry with materialThe combined organic parts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via FC (PE/EtOAc=5/1)

Sources & evidence

ORD record
ord-be4e00bc369445a4b2e299a17553fcd3
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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