2-Hydroxybenzonitrile → 2-Hydroxy-5-iodo-benzonitrile
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(S(O)(=O)=O)(F)(F)F.C1C(=O)N([I:25])C(=O)C1>CC#N>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([I:25])=[CH:6][C:3]=1[C:4]#[N:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-hydroxy-benzonitrile (47.6 g, 0.400 mmol) in CH3CN (500 mL) was added CF3SO3H (40 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 20 min, and then NIS (108 g, 0.48 mmol) was added. The mixture was stirred at room temperature overnight, then concentrated, diluted with H2O (300 mL) and extracted with EA (300 mL×3). Combined organic portions were dried over sodium sulfate, filtered and reconcentrated. Purification via column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) afforded the title product (80 g) as a white solid.
Workup
- stirringThe mixture was stirred at room temperature overnight
- concentrationconcentrated
- additiondiluted with H2O (300 mL)
- extractionextracted with EA (300 mL×3)
- dry with materialCombined organic portions were dried over sodium sulfate
- filtrationfiltered
- customPurification via column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)
Sources & evidence
- ORD record
- ord-208cf829163a47fbb7e5f1681ca406b2
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975400B2
Reaction notes
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