Sulfuric Acid → 4-Hydroxy-3-iodobenzonitrile

HRID 46333Notes

Reaction equation

HRID 46333 reaction equation
[I:1]N1C(=O)CCC1=O.S(=O)(=O)(O)O.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1>C(O)(=O)C>[OH:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[I:1]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 130194-CyanophenolHCID 120273N-Iodosuccinimide

Product 1

HCID 109558154-Hydroxy-3-iodobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Hydroxy-3-iodobenzonitrile was prepared by the method analogous to Preparation 341 above using N-iodosuccinimide, acetic acid, sulfuric acid and 4-Hydroxybenzonitrile. Purified by ISCO™ (80 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 3:7, by volume) to yield the title compound.

Workup

  1. custom4-Hydroxy-3-iodobenzonitrile was prepared by the method analogous to Preparation 341
  2. customPurified by ISCO™ (80 g SiO2)
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f36b3ff7d835481cbac8a5c7fe83c691
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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