Benzyl Bromide → 2-Ethenyl-4-fluoro-1-(phenylmethoxy)benzene

HRID 2178667노트

반응식

HRID 2178667 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[OH:10])=[CH2:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[O:10][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH2:2]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 53304460HCID 53304460, 화합물

생성물 1

HCID 683802772-Ethenyl-4-fluoro-1-(phenylmethoxy)benzene

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of 2-ethenyl-4-fluorophenol (C16) (1.03 g, 7.46 mmol) and potassium carbonate (3.12 g, 22.4 mmol) in acetone (35 mL) was treated with benzyl bromide (1.78 mL, 14.9 mmol) and stirred at reflux for 3 hours. The mixture was concentrated in vacuo, ethyl acetate (100 mL) was added and the mixture was washed with water (2×50 mL) and saturated aqueous sodium chloride solution (50 mL). The organic layer was dried over magnesium sulfate, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane) afforded the title compound as a colorless oil. Yield: 1.64 g, 7.23 mmol, 97%. GCMS m/z 228 (M+). 1H NMR (400 MHz, CDCl3) δ 5.08 (s, 2H), 5.33 (dd, J=11.1, 1.0 Hz, 1H), 5.76 (dd, J=17.8, 1.0 Hz, 1H), 6.85-6.95 (m, 2H), 7.11 (ddd, J=17.8, 11.1, 1.5 Hz, 1H), 7.23 (dd, J=9.4, 2.9 Hz, 1H), 7.33-7.48 (m, 5H).

후처리

  1. temperatureat reflux for 3 hours
  2. concentrationThe mixture was concentrated in vacuo, ethyl acetate (100 mL)
  3. additionwas added
  4. washthe mixture was washed with water (2×50 mL) and saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel chromatography (Gradient: 0% to 15% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-482ea8ee43864cf5ba104b3fd8ed7a50
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067934B2

반응 노트

불러오는 중…