HCID 16083237, compound → HCID 87326503, compound

HRID 2369761Notes

Reaction equation

[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])=[C:29]2[O:34][CH2:35][CH2:36][O:37][C:28]=12>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])=[C:29]4[O:34][CH2:35][CH2:36][O:37][C:28]=34)[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])=[C:29]3[O:34][CH2:35][CH2:36][O:37][C:28]=13)=[CH:15][CH:14]=2)[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 40 °C

Procedure

Air was removed from a solution of 2,7-diethynyl-9,9-dibutyl-9H-fluorene and 5-iodo-3,4-ethylenedioxythiophene-2-carboxaldehyde (Jessing, M.; Brandt, M.; Jensen, K. J.; Christensen, J. B.; Boas, U. J. Org. Chem. 2006, 71, 6734) (2.3 equiv) in toluene/Et3N (4/1) by blowing argon for 20 min. Then CuI (2×4 mol %) and Pd(PPh3)2Cl2 (2×4 mol %) 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 on silica gel (heptane/CH2Cl2 50:50 then 40:60) to yield 5,5′-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bis(3,4-ethylenedioxy-2-thiophenecarboxaldehyde).

Workup

customfor 20 min
customThe solvent was removed under reduced pressure
customthe crude product was purified by column chromatography on silica gel (heptane/CH2Cl2 50:50

Sources & evidence

ORD record: ord-afdc70acb64e40ec86ff3ec5210a652f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08709747B2

Reaction notes

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