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

HRID 550235노트

반응식

HRID 550235 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)]

출처 및 근거

ORD 기록
ord-6e649d73c71c447597e84b19ea0769e8
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943748B2

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