4-Nitrophenol → 2-Bromo-4-nitrophenol

HRID 1420824Notes

Reaction equation

HRID 1420824 reaction equation
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4]>C(O)(=O)C>[Br:1][C:10]1[CH:11]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 24408Bromine

Product 1

HCID 221092-Bromo-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (27 ml) was added dropwise to a stirred solution of 4-nitrophenol (50 g) in glacial acetic acid (400 ml) and the mixture was stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the residue was crystallised from dichloromethane:hexane to give the title compound as a colorless solid (67 g). 1H NMR (250 MHz, CDCl3) δ8.44 (1H, d, J 2.6 Hz), 8.16 (1H, dd, J 2.6, 8.9 Hz) and 7.13 (1H, d, J 9.0 Hz).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was crystallised from dichloromethane

Sources & evidence

ORD record
ord-08217bd84d2140b893585c66e6064cc6
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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