Potassium Iodide → 1-Cyclopentyl-3-iodobenzene

HRID 733199노트

반응식

HRID 733199 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 690505951-Cyclopentyl-3-iodobenzene수율 60%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매2회

반응 조건

온도
70 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-7b212281e1ab43318e94b1915f67d573
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589095B2

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