Boron trifluoride → 5-Bromo-3-methyl-2-(4-propylbenzyl)thiophene

HRID 1469199노트

반응식

HRID 1469199 반응식
[Br:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=O)=[C:4]([CH3:18])[CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(#N)C>[Br:1][C:2]1[S:6][C:5]([CH2:7][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[C:4]([CH3:18])[CH:3]=1

참가 물질

7

반응물 4

HCID 6356Boron trifluorideHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66691033(5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone

생성물 1

HCID 666908445-Bromo-3-methyl-2-(4-propylbenzyl)thiophene수율 94%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol) in DCM (9.4 mL) and ACN (9.4 mL) was added triethylsilane (1.42 mL, 8.85 mmol) followed by BF3 etherate (1.11 mL, 8.85 mmol) under nitrogen atmosphere at 0° C. The reaction mixture was allowed warmed to room temperature and stirred for 16 hours. The mixture was poured into a saturated K2CO3 solution (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide 5-bromo-3-methyl-2-(4-propylbenzyl)thiophene (46, 0.86 g, 2.77 mmol, 94%).

후처리

  1. extractionextracted with EtOAc (100 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated under vacuum
  4. customThe residue was further purified by silica column chromatography (Biotage)

출처 및 근거

ORD 기록
ord-458f1e71c49e483896ebd871bcd45c5a
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006187B2

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