Hydrogen Bromide → 5-Nitro-2-phenoxyphenol

HRID 1264034Notes

Reaction equation

HRID 1264034 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N+:16]([O-:18])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br>CC(O)=O>[N+:16]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:3]([OH:2])[CH:4]=1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 12867148HCID 12867148, compound

Product 1

HCID 128671525-Nitro-2-phenoxyphenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

3-methoxy-4-phenoxynitrobenzene(2 g, 8.15 mmol) was treated with 48% HBr (20 ml) and HOAc (20 ml), The reaction mixture was heated to 110 ° C. for 24 hours and then the reaction mixture was poured into ice and extracted with EtOAc, the organic layer was washed with brine, dried over Na2SO4. Removal of the solvent provided a brownish residue 5-Nitro-2-phenoxy-phenol which was taken to next step without further purification. (almost quantitative yield). 1H NMR (CDCl3): δ 7.91 (d,1H, 2.7 Hz), 7.72 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 7.43 (t, 2H, J=7.9 Hz), 7.28 (d, 1H, 7.9 Hz), 7.10 (d, 1H, J=8.3 Hz), 6.78 (d, 2H, J=8.9 Hz).

Workup

  1. additionthe reaction mixture was poured into ice
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-e1bada0c84144c65929732519139c535
Source dataset
uspto-grants-2003_04
Patent number
US06541481B2

Reaction notes

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