Potassium Iodide → 1-Cyclopentyl-3-iodobenzene

HRID 733199ノート

反応式

HRID 733199 の反応式
N([O-])=O.[Na+].Cl.[CH:6]1([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)N)[CH2:10][CH2:9][CH2:8][CH2:7]1.[I-:18].[K+].[OH-].[Na+]>O.Cl>[CH:6]1([C:11]2[CH:17]=[CH:16][CH:15]=[C:13]([I:18])[CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 690470023-Cyclopentylaniline hydrochloride

生成物 1

HCID 690505951-Cyclopentyl-3-iodobenzene収率 60%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回

反応条件

温度
70 °C

実験手順

A solution of sodium nitrite (558 mg, 8.1 mmol) in water (10 ml) was added over 5 minutes to a cooled (5° C.) solution of 3-cyclopentyl-aniline hydrochloride (1 g, 5.1 mmol) in 6N HCl (25 ml). After 50 minutes, a solution of potassium iodide (2.02 g, 12.2 mmol) in water (10 ml) was added over 5 minutes. The mixture was then heated for 1 h at 70° C. After cooling down to room temperature, the pH was set over 11 with 6N NaOH, and the mixture was extracted three times with CH2Cl2 (3×100 ml). The combined organic layers were washed with sodium thiosulfate (75 ml) then brine (75 ml) and dried over MgSO4. The solvent was removed under reduced pressure to give 1.23 g of crude material (HPLC: 67%) which was purified by chromatography over silica gel (eluent:cyclohexane) to yield the above titled compound as an oil: 825 mg, yield: 60%.

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionthe mixture was extracted three times with CH2Cl2 (3×100 ml)
  3. washThe combined organic layers were washed with sodium thiosulfate (75 ml)
  4. dry with materialbrine (75 ml) and dried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customto give 1.23 g of crude material (HPLC: 67%) which
  7. customwas purified by chromatography over silica gel (eluent:cyclohexane)

出典と根拠

ORDレコード
ord-7b212281e1ab43318e94b1915f67d573
出典データセット
uspto-grants-2009_09
特許番号
US07589095B2

反応ノート

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