1-Bromopropane → 2-Methyl-1-nitro-4-propoxybenzene

HRID 2174510Notes

Reaction equation

HRID 2174510 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH3:21]>CC(=O)CC>[CH3:1][C:2]1[CH:3]=[C:4]([O:11][CH2:19][CH2:20][CH3:21])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenol

Product 1

HCID 231345792-Methyl-1-nitro-4-propoxybenzeneYield 193.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Compound 403 (1.5 g, 9.8 mmol) was dissolved in 2-butanone (40 mL). Potassium carbonate (3.4 g, 24.5 mmol) was added and the solution heated at reflux. After 5 min, 1-bromopropane (18 μL, 5 mmol, 2 mL) was added drop-wise and the reaction mixture continued to stir for 18 h. The solvent was evaporated in vacuo and the crude residue was partitioned between EtOAc (150 mL) and saturated NaHCO3 (150 mL). The organic layer was separated, washed with brine (100 mL) and dried over Na2SO4. The resulting oil was purified by column chromatography (0% to 20% EtOAc/hexanes) to yield a yellow oil (1.89 g, 99%): TLC Rf 0.70 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.09-8.07 (d, 1H, J=8.76 Hz), 6.79-6.77 (m, 2H), 3.99-3.97 (t, 2H, J=6.54 Hz), 2.63 (s, 3H), 1.85-1.82 (sex, 2H, J=7.44 Hz), 1.06-1.04 (t, 3H, J=7.44 Hz). 13C NMR (150 MHz, CDCl3) δ 162.9, 142.2, 137.3, 127.8, 118.1, 112.4, 70.3, 22.60, 21.98, 10.6. Elemental analysis calculated for C10H13NO3.0.03 hexanes: C, 61.81; H, 6.84; N, 7.08. Found: C, 62.20; H, 6.78; N, 7.23.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux
  3. customThe solvent was evaporated in vacuo
  4. customthe crude residue was partitioned between EtOAc (150 mL) and saturated NaHCO3 (150 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. customThe resulting oil was purified by column chromatography (0% to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a9161d90109d4a6eba45e56f47b28fa6
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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