Hexane → Ethyl 2-fluoro-3-vinylbenzoate

HRID 658106노트

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HRID 658106 반응식
Br[C:2]1[C:3]([F:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:15].CCCCCC.[F-].[K+]>C([Sn](CCCC)(CCCC)C=C)CCC.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:13][C:3]1[C:2]([CH:14]=[CH2:15])=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

9

반응물 4

HCID 8058HexaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 17832538Ethyl 3-bromo-2-fluorobenzoate

생성물 1

HCID 68451554Ethyl 2-fluoro-3-vinylbenzoate수율 97%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 81998Tributylvinyltin용매

실험 절차

A 12.76 g portion of ethyl 3-bromo-2-fluorobenzoate was dissolved in 50 ml of Tol solution, 15.8 ml of tributyl(vinyl)tin, 236 mg of tris(dibenzylideneacetone)dipalladium and 1.25 ml of tri-tert-butylphosphine 10 wt % hexane solution were added thereto in order, and stirred at room temperature for 13 hours in an atmosphere of argon. This was diluted with 300 ml of diethyl ether, mixed with 25 g of potassium fluoride and 5 ml of purified water and stirred for 30 minutes, the insoluble matter was filtered using a Kiriyama funnel, and then the mother liquid was concentrated. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate=40:1) to obtain 10.3 g (97%) of ethyl 2-fluoro-3-vinylbenzoate (Reference Example 17-1).

후처리

  1. additionwere added
  2. stirringstirred for 30 minutes
  3. filtrationthe insoluble matter was filtered
  4. concentrationthe mother liquid was concentrated
  5. customThe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=40:1)

출처 및 근거

ORD 기록
ord-55c5804f981f4e779883f8eefa040d26
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076367B2

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