4-Nitrophenol → 2-Bromo-4-nitrophenol

HRID 1107277Notes

Reaction equation

HRID 1107277 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

4-Nitrophenol (50 g) was dissolved in glacial acetic acid (400 ml) and bromine (27 ml) was added dropwise and stirred for 18 hours. The reaction mixture was then evaporated to dryness, and the crude product crystallised from dichloromethane:hexane to yield the title compound as white crystals (67 g). 1H NMR (250 MHz, CDCl3) δ 8.44 (1H, d, J=2.6 Hz), 8.16 (1H, dd, J=2.6 and 8.9 Hz) and 7.13 (1H, d, J=9.0 Hz).

Workup

  1. customThe reaction mixture was then evaporated to dryness
  2. customthe crude product crystallised from dichloromethane

Sources & evidence

ORD record
ord-7703254c4722403ab5d7a84e894cdb30
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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