Hydrochloric Acid → 3,3'-Dihexyl-2,2'-bithiophene

HRID 278832노트

반응식

HRID 278832 반응식
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]1[S:16][CH:17]=[CH:18][C:19]=1Br.Cl>C(OCC)C.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]1[S:16][CH:17]=[CH:18][C:19]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8190873,3'-Dibromo-2,2'-bithiopheneHCID 178444609HCID 178444609, 화합물

생성물 1

HCID 114844383,3'-Dihexyl-2,2'-bithiophene수율 100.1%

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

Hexylmagnesium bromide (100 ml, 2 M solution in diethyl ether, 200 mol) was added dropwise to a solution of 3,3′-dibromo-2,2′-bithiophene (15 g, 46.6 mmol) and Ni(dppp)Cl2 (0.5 g, 0.1 mmol) in 100 ml of diethyl ether at 0° C. The reaction was slightly exothermic and a red brown coloration was observed. After stirred and heated for 24 h, the reaction mixture was cautiously poured into a mixture of crushed ice and diluted HCl solution and extracted with ether. The combined extracts were dried over anhydrous MgSO4 and filtered. After removal of the solvent, the residue was vacuum-distilled to give a clear viscous oil (15.6 g, 81%). 1H-NMR (CDCl3, ppm): δ7.25 (d, 2H, J=5 Hz), 6.96 (d, 2H, J=5 Hz), 2.50 (t, 4H), 1.54 (m, 4H), 1.23 (m, 12H), 0.85 (t, 6H).

후처리

  1. temperatureheated for 24 h
  2. extractionextracted with ether
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customAfter removal of the solvent
  6. distillationthe residue was vacuum-distilled

출처 및 근거

ORD 기록
ord-843b4f64706a48bc96d032b421ba5e52
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06361717B1

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