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

HRID 2174510ノート

反応式

HRID 2174510 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 231345792-Methyl-1-nitro-4-propoxybenzene収率 193.6%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a9161d90109d4a6eba45e56f47b28fa6
出典データセット
uspto-grants-2015_06
特許番号
US09061994B1

反応ノート

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