Sodium Carbonate → 4-(3,5-Bis-trifluoromethyl-benzyl)-2-methylnitrobenzene

HRID 1640097노트

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HRID 1640097 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C(OCC)(=O)C>[F:13][C:14]([F:28])([F:29])[C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)[CH2:5][C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 1562653,5-Bis-trifluoromethylphenylboronic acid

생성물 1

HCID 592295044-(3,5-Bis-trifluoromethyl-benzyl)-2-methylnitrobenzene수율 83.3%

시약·촉매·용매 3

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-methyl-4-nitrobenzyl chloride (0.27 g), 3,5-bis-(trifluoromethyl)phenylboronic acid (0.45 g), tetrakis(triphenylphosfine)palladium (0.1 g) and sodium carbonate (0.48 g) in water (2 ml) and 1,2-dimethoxyethane (10 ml) was stirred under an argon atmosphere at 85° C. for 2 hours. After cooling, the reaction solution was diluted with ethyl acetate and further stirred for 10 minutes by adding water thereto. After washing the organic layer with a saturated salt solution, it was dried over anhydrous magnesium sulfate. The solution was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain 4-(3,5-bis-trifluoromethyl-benzyl)-2-methyl-nitrobenzene (0.44 g).

후처리

  1. temperatureAfter cooling
  2. washAfter washing the organic layer with a saturated salt solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solution was distilled off under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8c6e98deb47f4c6d8b0369cd3fdafd97
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110689B2

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