Isopropyl iodide → 1-Bromo-3-(isopropylsulfanyl)benzene

HRID 29269

反応式

HRID 29269 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:16]([CH3:18])[CH3:17]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH:16]([CH3:18])[CH3:17])[CH:3]=1

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

生成物 1

HCID 179787721-Bromo-3-(isopropylsulfanyl)benzene収率 93.17%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3-Bromobenzenethiol (1 g, 5.3 mmol) was added to acetone (25 mL). Next was added potassium carbonate (1.46 g, 10.58 mmol) and 2-iodopropane (1.17 g, 6.88 mmol). This was refluxed for 5 h. Reaction was then cooled to rt and filtered through a pad of Celite. The organic was then concentrated in vacuo and taken up in ether at which time a white precipitate crashed out. The organic was then re-filtered through the same celite plug and concentrated in vacuo to provide 1.14 g (93.17%) of 1-bromo-3-isopropylsulfanyl-benzene as an oil. 1H-NMR (methylene chloride -d2) δ 7.54 (s, 1H), 7.37-7.31 (m, 2H), 7.18 (t, J=7.9 Hz, 1H), 3.50-3.36 (m, 1H), 1.31 (d, J=6.1 Hz, 6H); LC-MS RT: 4.15, [M+H]+: 233.2.

後処理

  1. temperatureThis was refluxed for 5 h
  2. customReaction
  3. filtrationfiltered through a pad of Celite
  4. concentrationThe organic was then concentrated in vacuo
  5. filtrationThe organic was then re-filtered through the same celite plug
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-93ef0c03cac1401c888e831169151d18
出典データセット
uspto-grants-2008_09
特許番号
US07420066B2

関連ノート

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