2-Chloro-3-nitropyridine → 2-Mesityl-3-nitropyridine

HRID 890191

반응식

HRID 890191 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 796132-Chloro-3-nitropyridineHCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acid

생성물 1

HCID 222494912-Mesityl-3-nitropyridine수율 78.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 107951,1-Dimethoxyethane용매

실험 절차

A solution of 2-chloro-3-nitropyridine (5.0 g, 31.5 mmol), mesitylboric acid (5.65 g, 34.7 mmol), Pd(PPh3)4 (1.82 g, 1.58 mmol) and barium hydroxide octahydrate (14.9 g, 47.3 mmol) in 2,2-dimethoxyethane (150 mL) and water (25 mL) was heated under reflux for one day. The mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatogrpahy (10% ethyl acetate/hexane), to give the title compound (5.99 g) as pale yellow oil.

후처리

  1. temperatureunder reflux for one day
  2. filtrationThe mixture was filtered through Celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatogrpahy (10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f7a60431059348038138f2e337d17172
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995163B2

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