Sulfuric Acid → 2-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester

HRID 1910761Notes

Reaction equation

HRID 1910761 reaction equation
[CH:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2].[Br:16][CH2:17][CH2:18]O.S(=O)(=O)(O)O>O>[Br:16][CH2:17][CH2:18][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 108982-BromoethanolHCID 671058552-Isopropyl-4-nitro-benzoic acid

Product 1

HCID 671063212-Isopropyl-4-nitro-benzoic acid 2-bromo-ethyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-isopropyl-4-nitro-benzoic acid (0.23 g, 1.10 mmol), 2-bromoethanol (1.0 mL, 14.1 mmol) and conc. sulfuric acid (0.2 mL) was heated at 80° C. overnight. The mixture was cooled to r.t., diluted with water and extracted twice with ethyl acetate. The organic phase was washed with sat. sodium bicarbonate solution, water and brine then dried over sodium sulfate and concentrated. The crude product was purified by column chromatography on silica (60-120 mesh), eluting with 7% ethyl acetate/petroleum ether, to afford 2-isopropyl-4-nitro-benzoic acid 2-bromo-ethyl ester (0.24 g, 69%) as a colourless oil.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. extractionextracted twice with ethyl acetate
  3. washThe organic phase was washed with sat. sodium bicarbonate solution, water and brine
  4. dry with materialthen dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica (60-120 mesh)
  7. washeluting with 7% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-696b532999a847d891fc6af5128c87ce
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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