Sulfuric Acid → 5-Bromo-2-nitrophenol

HRID 2036742Notes

Reaction equation

HRID 2036742 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])([O-])=[O:7].[K+].[Br:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1>O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([N+:6]([O-:9])=[O:7])=[C:14]([OH:18])[CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 115633-BromophenolHCID 24434Potassium Nitrate

Product 1

HCID 139704965-Bromo-2-nitrophenolYield 18.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of concentrated sulfuric acid (32.6 mL) in water (105 mL) was added potassium nitrate (51.5 g, 509 mmol) at 10° C. The reaction mixture was stirred for 5 min before adding 3-bromophenol (49.35 g, 285 mmol) dropwise so that the temperature of the reaction was maintained around 10° C. The reaction mixture was stirred at ambient temperature for an additional 2 h, diluted with water (350 mL) and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography (SiO2, 19:1 hexanes/ethyl acetate) to give 5-bromo-2-nitrophenol (11.3 g, 18%) as a yellow-green solid: 1H NMR (DMSO-d6, 300 MHz) δ 11.44 (s, 1H), 7.84 (d, J=8.7 Hz, 1H), 7.33 (d, J=2.1 Hz, 1H), 7.18 (dd, J=8.7, 2.1 Hz, 1H).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for an additional 2 h
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (SiO2, 19:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f5e9e931f5ad4cf8871a048e5ca436e2
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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