Sulfuric Acid → 4'-Hydroxy-3'-iodobiphenyl-3-carbonitrile

HRID 1619721Notes

Reaction equation

HRID 1619721 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[I:21]N1C(=O)CCC1=O>ClCCl.C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[CH:9]=2)=[CH:6][C:7]=1[I:21]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 120273N-IodosuccinimideHCID 37790963-(4-Hydroxyphenyl)benzonitrile

Product 1

HCID 580423194'-Hydroxy-3'-iodobiphenyl-3-carbonitrileYield 77%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

4′-Hydroxybiphenyl-3-carbonitrile (Preparation 121, 570 mg, 2.92 mmol) was dissolved in dichloromethane (10 mL) and acetic acid (10 mL). Then concentrated sulfuric acid (0.30 mL) and N-iodosuccinimide (657 mg, 2.92 mmol) were added at 0° C. (ice-bath cooling) and the reaction was allowed to warm to room temperature over 2 hours. The mixture was partitioned between ethyl acetate (30 mL) and water (15 mL). The organic layer was separated and dried over anhydrous MgSO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in heptane to give the title compound (720 mg, 77%).

Workup

  1. temperature(ice-bath cooling)
  2. customThe mixture was partitioned between ethyl acetate (30 mL) and water (15 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel eluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-e1747cc4a81d43b0b587e000e56a7d36
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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