1-Naphthalenamine, 5-nitro- → 1-Fluoro-5-nitronaphthalene

HRID 880471

반응식

HRID 880471 반응식
N([O-])=O.[Na+].[N+:5]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:13]2N)([O-:7])=[O:6].[F:19][P-](F)(F)(F)(F)F.[H+]>O>[F:19][C:13]1[C:14]2[C:9](=[C:8]([N+:5]([O-:7])=[O:6])[CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 767591-Naphthalenamine, 5-nitro-HCID 16211447Hexafluorophosphoric acidHCID 23668193Sodium Nitrite

생성물 1

HCID 217302841-Fluoro-5-nitronaphthalene수율 37%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-5 °C

실험 절차

Sodium nitrite (660 mg, 9.57 mmol) was added portionwise to a suspension of 5-nitronaphthalen-1-amine (1.2 g, 6.38 mmol) in a 1:1 mixture of water/concentrated hydrochloric acid (10 mL) at −5° C. The mixture was stirred for 15 min at −5° C. and a 60% w/w hexafluoro phosphoric acid solution (6 mL) was added. The brown precipitate was filtered and washed with cold water and diethyl ether and then allowed to dry in vacuo. The resulting solid was suspended in toluene and heated to 110° C. for 2 h before the mixture was then allowed to cool to ambient temperature and the solvent removed in vacuo to afford the crude product. Purification by column chromatography over silica gel (100-200 mesh) using petroleum ether as eluent afforded 1-fluoro-5-nitro-naphthalene (450 mg, 37%) as a yellow solid.

후처리

  1. filtrationThe brown precipitate was filtered
  2. washwashed with cold water and diethyl ether
  3. customto dry in vacuo
  4. temperatureheated to 110° C. for 2 h before the mixture
  5. temperatureto cool to ambient temperature
  6. customthe solvent removed in vacuo
  7. customto afford the crude product
  8. customPurification by column chromatography over silica gel (100-200 mesh)

출처 및 근거

ORD 기록
ord-e7c74a2612ca4b13a40f0adf05f393d4
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993574B2

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