Hexane → Ethyl 2-fluoro-3-vinylbenzoate

HRID 658106ノート

反応式

HRID 658106 の反応式
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]

参加物

9

反応物 4

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

生成物 1

HCID 68451554Ethyl 2-fluoro-3-vinylbenzoate収率 97%

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 81998Tributylvinyltin溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-55c5804f981f4e779883f8eefa040d26
出典データセット
uspto-grants-2011_12
特許番号
US08076367B2

反応ノート

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