4-Nitrophenol → 2-Bromo-4-nitrophenol

HRID 565376Notes

Reaction equation

HRID 565376 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11]Br>C(O)(=O)C>[Br:11][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[OH:10]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 24408Bromine

Product 1

HCID 221092-Bromo-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

to a solution of 4-nitrophenol (75 g, 0.54 mol) in glacial acetic acid (700 ml) was added bromine (40 ml). The solution was stirred at room temperature under an atmosphere of nitrogen for 24 hours. The solvent was evaporated under reduced pressure and the residue was recrystallized from dichloromethane to give the title compound. 1H NMR (250 MHz, CDCl3) δ 8.45 (1H, d, J 2.7 Hz), 8.16 (1H, dd, J 9.0 Hz and 2.6 Hz), 7.13 (1H, d, J 9.1 Hz), and 6.18 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-cd814e41bbe7443dab23abbadca80e8c
Source dataset
uspto-grants-2001_01
Patent number
US06172077B2

Reaction notes

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