Nitric Acid → 1-Bromo-4-isopropyl-2-nitrobenzene

HRID 605378Notes

Reaction equation

HRID 605378 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1>>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:14])[CH3:13])=[CH:8][C:7]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 114621-Bromo-4-isopropylbenzene

Product 1

HCID 215318151-Bromo-4-isopropyl-2-nitrobenzeneYield 84%

Procedure

To fuming nitric acid (5 mL) cooled to 5° was added neat 4-bromoisopropylbenzene (1.0 g, 5.023 mmol) dropwise at such a rate that the reaction temperature remained below 10°. The reaction was stirred for 2 hours at 5-10°, quenched with ice (50 g), extracted with ethyl acetate (50 mL), and the organic extract was washed with water (2×25 mL) and brine (25 mL), then dried over magnesium sulfate filtered and concentrated by rotary evaporation. The residue was purified by silica gel flash chromatography eluting with 5:95 ethyl acetate/hexanes to afford the title compound as a light yellow solid (1.03 g, 4.22 mmol, 84%). 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.27 (d, J=6.99 Hz, 6 H) 2.75-3.23 (m, 1 H) 7.29 (dd, J=8.82, 2.21 Hz, 1 H) 7.63 (d, J=8.09 Hz, 1 H) 7.69 (d, J=2.21 Hz, 1 H); MS (DCI) m/z 261/263 (M+NH4)−.

Workup

  1. customremained below 10°
  2. customquenched with ice (50 g)
  3. extractionextracted with ethyl acetate (50 mL)
  4. extractionthe organic extract
  5. washwas washed with water (2×25 mL) and brine (25 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by silica gel flash chromatography
  10. washeluting with 5:95 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9e8dcab41e934e01a08d81180d599ef0
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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