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

HRID 2178667ノート

反応式

HRID 2178667 の反応式
[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]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 53304460HCID 53304460、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-482ea8ee43864cf5ba104b3fd8ed7a50
出典データセット
uspto-grants-2015_06
特許番号
US09067934B2

反応ノート

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