2-Bromophenol → 2-Bromo-6-nitrophenol

HRID 1814201Notes

Reaction equation

HRID 1814201 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N+:9]([O-])([O-:11])=[O:10].[Na+]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:8]

Participants

5

Reactant 2

HCID 72442-BromophenolHCID 24268Sodium Nitrate

Product 1

HCID 135454532-Bromo-6-nitrophenolYield 30.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

2-Bromophenol (50.0 g, 0.29 mol) was added slowly to a cold (10° C.) solution of sodium nitrate (36.9 g, 0.43 mol) in conc. sulfuric acid (79 g) and water (100 mL) and the resulting mixture was allowed to stir at room temperature for 2 h. Water (400 mL) was added and the resulting mixture was extracted with diethyl ether and the extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane). The partly purified product was triturated with hexane to afford the title compound (19.2 g, 30%) as a bright, yellow solid. 1H NMR (300 MHz, CDCl) δ 11.10 (S, 1h), 8.13 (d, J=7.9 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 6.90 (t,J=7.9 Hz, 1H).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. dry with materialthe extract was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica gel, 5% ethyl acetate/hexane)
  6. customThe partly purified product was triturated with hexane

Sources & evidence

ORD record
ord-7fd1630b8da048ac81b1288b9594d708
Source dataset
uspto-grants-2005_04
Patent number
US06875786B2

Reaction notes

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