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5-Bromo-2-nitrobenzotrifluoride → HCID 22313797, 화합물

HRID 965954
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HRID 965954 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]([O:22]CC)=[CH2:21])CCC.[Li+].[Cl-]>O1CCOCC1.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>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:20](=[O:22])[CH3:21])=[CH:3][C:4]=1[C:11]([F:14])([F:13])[F:12])([O-:10])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 1361715-Bromo-2-nitrobenzotrifluorideHCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

생성물 1

HCID 22313797HCID 22313797, 화합물수율 94%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 31275
1,4-Dioxane
용매

실험 절차

A mixture of 4-bromo-1-nitro-2-(trifluoromethyl)benzene (1.87 g, 6.93 mmol), tributyl(1-ethoxyvinyl)tin (3.00 g, 8.31 mmol), Pd(PPh3)4 (801 mg, 0.693 mmol), and LiCl (734 mg, 17.3 mmol) in 1,4-dioxane (50 ml) was heated to reflux for 7 hours. The mixture was filtered through a pad of Celite with ethyl acetate. The filtrate was washed with water (100 ml) and brine (100 ml), dried over MgSO4, and evaporated in vacuo. To the obtained residue were added 2N HCl (20 ml) and THF (60 ml). The mixture was stirred at room temperature for 1.5 hours. Saturated aqueous NaHCO3 (60 ml) was added and the aqueous layer was extracted with ethyl acetate (100 ml×2). The combined organic layer was dried over MgSO4, and evaporated in vacuo. The resulting residue was chromatographed over slica gel with hexane/ethyl acetate (3:1) to give 1.51 g (94%) of the title compound as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. filtrationThe mixture was filtered through a pad of Celite with ethyl acetate
  4. washThe filtrate was washed with water (100 ml) and brine (100 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. additionTo the obtained residue were added 2N HCl (20 ml) and THF (60 ml)
  8. additionSaturated aqueous NaHCO3 (60 ml) was added
  9. extractionthe aqueous layer was extracted with ethyl acetate (100 ml×2)
  10. dry with materialThe combined organic layer was dried over MgSO4
  11. customevaporated in vacuo
  12. customThe resulting residue was chromatographed over slica gel with hexane/ethyl acetate (3:1)

출처 및 근거

ORD 기록
ord-f156782277ac48119956242e6b5a8b91
출처 데이터셋
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06951876B2

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