Water → 2-[4-(1-Methyl-hexyloxy)-phenyl]-thiophene

HRID 1725092노트

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HRID 1725092 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.C([Sn]([C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)(CCCC)CCCC)CCC.O>CN(C=O)C>[CH3:15][CH:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([C:29]2[S:30][CH:31]=[CH:32][CH:33]=2)=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 962WaterHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 200967851-Bromo-4-(1-methyl-hexyloxy)-benzene

생성물 1

HCID 575620232-[4-(1-Methyl-hexyloxy)-phenyl]-thiophene수율 44.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Tetrakistriphenylphosphinpalladium(0), (20.45 g, 17.70 mmol) is suspended in anhydrous DMF (400 mL) in a 2000 mL 3-necked flask with magnetic stirrer and condenser under an argon atmosphere. To this, 1-bromo-4-(1-methyl-hexyloxy)-benzene (240.00 g, 884.96 mmol) and tri-n-butylstannylthiophene (330.24 g, 884.96 mmol) are added. The resulting solution is stirred at 100° C. for 68 hours. After cooling to room temperature the mixture is poured into water (2000 mL) and divided into two portions of the same volume. Extraction with n-hexane (3×300 mL) results in two layers and an emulsion between those two layers. The organic layers are separated, combined, washed with diluted sodium chloride solution (2×400 mL) and dried (MgSO4). After removal of solvent by rotary evaporation most of the byproducts are removed by distillation (p=10−3 millibar, maximum temperature Tmax=130° C.). The residue is subjected to filtration using a layer of SiO2 (30×10 cm) and n-hexane as eluent. After removal of solvent, a yellowish oil (107.88 g, about 44%) with sufficient purity for synthetic purposes is obtained.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionExtraction with n-hexane (3×300 mL)
  3. customresults in two layers
  4. customThe organic layers are separated
  5. washwashed with diluted sodium chloride solution (2×400 mL)
  6. dry with materialdried (MgSO4)
  7. customAfter removal of solvent
  8. customby rotary evaporation most of the byproducts
  9. customare removed by distillation (p=10−3 millibar, maximum temperature Tmax=130° C.)
  10. filtrationThe residue is subjected to filtration
  11. customAfter removal of solvent

출처 및 근거

ORD 기록
ord-e817ddfd268d4f3ab725cf8857edb119
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488834B2

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