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

HRID 2174510노트

반응식

HRID 2174510 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a9161d90109d4a6eba45e56f47b28fa6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061994B1

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