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

HRID 1469199ノート

反応式

HRID 1469199 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-458f1e71c49e483896ebd871bcd45c5a
出典データセット
uspto-grants-2015_04
特許番号
US09006187B2

反応ノート

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