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Triethylsilane → 3-Bromo-(5-ethyl-2-thienylmethyl)benzene

HRID 1625768
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HRID 1625768 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)O)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:10]2[S:11][C:12]([CH2:15][CH3:16])=[CH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 611008623-Bromophenyl-5-ethyl-2-thienylmethanol

생성물 1

HCID 469304303-Bromo-(5-ethyl-2-thienylmethyl)benzene수율 93.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

The above 3-bromophenyl-5-ethyl-2-thienylmethanol (2.90 g) was dissolved in dichloromethane (38 ml), and the mixture was cooled to −78° C. under argon atmosphere. To the mixture were added triethylsilane (6.18 ml) and boron trifluoride diethyl ether complex (2.45 ml), and the mixture was gradually warmed to room temperature over a period of one hour. The mixture was basified with a saturated aqueous sodium hydrogen carbonate solution, and the dichloromethane layer was collected, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give the desired 3-bromo-(5-ethyl-2-thienylmethyl)benzene (2.57 g) as a colorless syrup. APCI-Mass m/Z 281/283 (M+H).

후처리

  1. temperaturethe mixture was gradually warmed to room temperature over a period of one hour
  2. customthe dichloromethane layer was collected
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane)

출처 및 근거

ORD 기록
ord-454deec6463c4a85bb1ea1c4960b92fb
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785403B2

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