2-Bromonaphthalene → 2-(4-Nitrophenylthio)naphthalene

HRID 55075

반응식

HRID 55075 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

참가 물질

6

반응물 3

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

생성물 1

HCID 189716852-(4-Nitrophenylthio)naphthalene수율 12%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 1049Pyridine용매

실험 절차

2-Bromonaphthalene (0.08 moles, 16.6 g), 4-nitrothiophenol (0.08 moles, 12.4 g), potassium carbonate (0.1 moles, 13.4 g), copper bronze (6.0 g) and cuprous chloride (0.02 moles, 2.0 g) were heated under reflux for 4 days in 300 ml pyridine. The solution was filtered hot, concentrated, dissolved in ethyl acetate and washed thoroughly with 2N HCl and water. The solution was dried over sodium sulfate, concentrated and purified by HPLC over silica gel eluted with 5% ethyl acetate in hexane. The product was recrystallized from ethyl acetate and hexane to yield 2-(4-nitrophenylthio)naphthalene 2.6 g, 12% in the first crop. Mass spec. (FD) 281.

후처리

  1. filtrationThe solution was filtered hot
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed thoroughly with 2N HCl and water
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by HPLC over silica gel
  8. washeluted with 5% ethyl acetate in hexane
  9. customThe product was recrystallized from ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-09578c9c56544be3ba3e104ce53517cd
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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