4-Nitrophenol → 2-Bromo-4-nitrophenol

HRID 1420690Notes

Reaction equation

HRID 1420690 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 solution of 4-nitrophenol (50 g) in glacial acetic acid (400 ml) and the mixture stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and the residue was crystallised from dichloromethane/hexane. The solid was collected and dried in vacuo to give the title compound as a colorless solid (67 g); δH (250MHz, CDCl3) 7.13 (1H, d, J 8.9 Hz, 6-H), 8.16 (1H, dd, J 2.6, 8.9 Hz, 5-H), 8.44 (1H, d, J 2.6 Hz, 3-H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was crystallised from dichloromethane/hexane
  3. customThe solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-01700aca876e485e965b4ec41ad114e3
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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