Potassium Carbonate → 1-Bromo-3-ethynylbenzene

HRID 2240981

反応式

HRID 2240981 の反応式
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([C:14]#[C:15][Si](C)(C)C)[CH:11]=[CH:12][CH:13]=1>CO>[Br:7][C:8]1[CH:9]=[C:10]([C:14]#[CH:15])[CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 3683324((3-Bromophenyl)ethynyl)trimethylsilane

生成物 1

HCID 114808181-Bromo-3-ethynylbenzene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To each of 2 one-liter flasks were charged K2CO3 (68 g, 493 mmol), a large magnetic stirbar and MeOH (250 mL). Stirring was begun on both reaction mixtures and once it was satisfied that they were stirring without any problems, 3-bromophenyltrimethylsilylacetylene (12.5 g, 49.3 mmol, 10.5 mL) was added to each reaction vessel and the mixtures were refluxed overnight. The reaction mixtures were filtered and the filter cakes were washed with MeOH. The combined filtrate was concentrated in vacuo, diluted with hexanes, and washed with water twice. The organic layer was concentrated to give a yellow oil. Flash chromatography (SiO2, Hexanes), provided 9.1 g, 50%, of the title compound as a colorless to light yellow oil. 1H NMR 500 MHz (CDCl3) δ 3.08 (s, 1H); 7.16 (t, 1H, J=7.89 Hz); 7.38 (dt, 1H, J=7.77 Hz, 2.44 Hz); 7.44-7.47 (m, 1H); 7.61 (t, 1H, J=1.68 Hz).

後処理

  1. customwas begun on both reaction mixtures and once it
  2. additionwas added to each reaction vessel
  3. temperaturethe mixtures were refluxed overnight
  4. customThe reaction mixtures
  5. filtrationwere filtered
  6. washthe filter cakes were washed with MeOH
  7. concentrationThe combined filtrate was concentrated in vacuo
  8. additiondiluted with hexanes
  9. washwashed with water twice
  10. concentrationThe organic layer was concentrated
  11. customto give a yellow oil

出典と根拠

ORDレコード
ord-09ca21e5e3024d969bbb3a9ff72b3184
出典データセット
uspto-grants-2010_05
特許番号
US07723368B2

関連ノート

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