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2-Thiophenecarboxaldehyde, 5-iodo- → HCID 86678076, 화합물

HRID 2369760
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HRID 2369760 반응식
[C:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([C:16]#[CH:17])=[CH:10][CH:11]=3)[C:6]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[CH:4]=1)#[CH:2].I[C:27]1[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:22]([C:6]1([CH2:18][CH2:19][CH2:20][CH3:21])[C:7]2[CH:8]=[C:9]([C:16]#[C:17][C:27]3[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=3)[CH:10]=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][C:3]([C:1]#[C:2][C:27]1[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=1)=[CH:15][CH:14]=2)[CH2:23][CH2:24][CH3:25]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 30143612-Thiophenecarboxaldehyde, 5-iodo-HCID 86678075HCID 86678075, 화합물

생성물 1

HCID 86678076HCID 86678076, 화합물수율 97.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매
HCID 22504574
Toluene triethylamine
용매

반응 조건

온도
40 °C

실험 절차

Air was removed from a solution of 2,7-diethynyl-9,9-dibutyl-9H-fluorene (0.150 g, 0.460 mmol) and 5-iodothiophene-2-carboxaldehyde (Wu, L.-H.; Chu, C.-S.; Janarthanan, N.; Hsu, C.-S. J. Polym. Res. 2000, 7, 125-134) (0.251 g, 1.06 mmol) in 6.5 mL of toluene/Et3N (4/1) by blowing argon for 20 min. Then CuI (7.0 mg, 0.0037 mmol) and Pd(PPh3)2Cl2 (27 mg, 0.0039 mmol) were added, and deaeration was continued for 10 min. Thereafter the mixture was stirred at 40° C. for 16 h. The solvent was removed under reduced pressure, and the crude product was purified by column chromatography (heptane/CH2Cl2 50:50 then 40:60) to yield 245 mg (97%) of 5,5′-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bis-2-thiophenecarboxaldehyde; 1H NMR (300.13 MHz, CDCl3) δ 9.80 (s, 2H), 7.61 and 7.26 (AX, JAX=3.9 Hz, 4H), 7.62 (d, J=8.5 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 7.45 (s, 2H), 1.93 (m, 4H), 1.02 (m, 4H), 0.60 (t, J=7.3 Hz, 6H), 0.51 (m, 4H); 13C NMR (75.46 MHz, CDCl3) δ 182.4, 151.4, 143.9, 141.4, 136.1, 133.0, 132.5, 131.0, 126.0, 120.9, 120.4, 98.9, 82.6, 55.3, 40.1, 25.9, 23.0, 13.8; HRMS (ESI) calcd for C35H30O2S2 (M+·) m/z 546.16872. found 546.1687.

후처리

  1. customfor 20 min
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography (heptane/CH2Cl2 50:50

출처 및 근거

ORD 기록
ord-bafe06b25218426e81261ae1df4244e6
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08709747B2

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