2-Bromothiophene → 2,2':5',2'',5'',2'''-Quaterthiophene

HRID 742937

반응식

HRID 742937 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Mg]Br.Br[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.[Mg].Br[C:16]1[S:20][C:19]([C:21]2[S:22][C:23](Br)=[CH:24][CH:25]=2)=[CH:18][CH:17]=1>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:11]1[S:10][C:9]([C:16]2[S:20][C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 138512-BromothiopheneHCID 6389085,5'-Dibromo-2,2'-bithiopheneHCID 5462224MagnesiumHCID 178418438HCID 178418438, 화합물

생성물 1

HCID 3954932,2':5',2'',5'',2'''-Quaterthiophene

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

Thienylmagnesiumbromide, made from 13 gr (80 mmol) of T-Br and 2.43 gr (100 mmol) of magnesium in 50 ml of anhydrous ether, was added to a solution of 11.71 gr (36 mmol) of 5,5'-dibromo-2,2'-bithiophene and 100 mg (0.18 mmol) of Ni(dppp)Cl2 in 150 ml of ether. The reaction mixture was refluxed for 4 hours and subsequently poured on an ice/dilute hydrochloric acid mixture. The product was extracted with toluene and recrystallized from a mixture of toluene and ethanol. The resulting orange powder was dried in vacuo. Yield: 6,75 gr (20 mmol, 57%) of T4. M.p.: 203° C. (litt: 212). Elemental analysis: found% (theory%) C 56.49 (58.15), H 3.05 (3.05), S 37.0 (38.8). 1H-NMR (300 MHz, CDCl3): ∂=7.23 (2H, dd, J=5.0 and 1.0 Hz), ∂=7.19 (2H, dd, J=3.7 and 1.0 Hz), ∂=7.08 (4H, s), ∂=7.03 (2H, dd, J=5.0 and 3.7 Hz). M/z: 330 D (M.W.=330).

후처리

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. extractionThe product was extracted with toluene
  3. customrecrystallized from a mixture of toluene and ethanol
  4. customThe resulting orange powder was dried in vacuo

출처 및 근거

ORD 기록
ord-5c36b1f41c744aadbd163bf24bf25ecd
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556524

연결된 노트

불러오는 중…