Triethylsilane → 2-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiophene

HRID 550235ノート

反応式

HRID 550235 の反応式
C([SiH](CC)CC)C.[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH:19]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=3[CH:22]=2)O)[CH:10]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=3[CH:22]=2)[CH:10]=1

参加物

5

反応物 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67156712(4-Bromo-naphthalen-2-yl)-(5-fluorobenzo[b]-thiophen-2-yl)methanol

生成物 1

HCID 671565772-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiophene収率 215.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a nitrogen stream, triethylsilane (0.18 ml, 2.11 mmol) and a boron trifluoride-diethyl ether complex (0.25 ml, 1.94 mmol) were added to a solution of (4-bromo-naphthalen-2-yl)-(5-fluorobenzo[b]-thiophen-2-yl)methanol (260 mg, 0.65 mmol) in methylene chloride (10 ml) at 0° C. and the mixture was stirred a room temperature for two hours. A saturated sodium hydrogen carbonate aqueous solution was added and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:100)] to obtain the title compound (520 mg, 80%).

後処理

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:100)]

出典と根拠

ORDレコード
ord-6e649d73c71c447597e84b19ea0769e8
出典データセット
uspto-grants-2011_05
特許番号
US07943748B2

反応ノート

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