4-Cyanophenol → 3-Bromo-4-hydroxybenzonitrile

HRID 2390142Notes

Reaction equation

HRID 2390142 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[Br:10]N1C(=O)CCC1=O>C(O)(=O)C>[Br:10][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[OH:9])[C:1]#[N:2]

Participants

4

Reactant 2

HCID 130194-CyanophenolHCID 67184N-bromobutanimide

Product 1

HCID 753413-Bromo-4-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-cyanophenol (30.0 g, 252 mmol) in acetic acid (450 ml) was treated with N-bromosuccinimide (44.8 g, 252 mmol). The reaction mixture was stirred at RT for 18 h, filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography (silica) eluting with chloroform and methanol (99:1) to afford the title compound as a brown solid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude material was purified by column chromatography (silica)
  4. washeluting with chloroform and methanol (99:1)

Sources & evidence

ORD record
ord-82a6c38b28514f37bd9e52b2204e038d
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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