Triethylamine → 2-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiophene

HRID 83970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83970
BrC1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[CH:29]#[C:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[CH2:39](N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:30]([C:29]1[S:18][C:5]2[C:6]3[S:14][C:13]4[C:12]5[S:15][CH:16]=[CH:17][C:11]=5[S:10][C:9]=4[C:7]=3[S:8][C:4]=2[C:3]=1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 129971-DecyneHCID 669248622-Bromo-3-decanyldithieno[2,3-d:2',3'-d']thieno[3,2-b:4,5-b']dithiophene

Produkt 1

HCID 669248432-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiopheneAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

2-Bromo-3-decanyldithieno[2,3-d:2′,3′-d′]thieno[3,2-b:4,5-b′]dithiophene (2.16 g, 4.6 mmol) (106) is mixed with 1-decyne (1.27 g, 9.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol) and copper(I) iodide (0.087 g, 0.46 mmol) in triethylamine (50 mL). This mixture is bubbled with nitrogen for 5 minutes and then heated to 130° C. under argon for 16 hours. The triethylamine is evaporated and hexane (150 mL) is added. This mixture is filtered to remove solid salts. The organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent is removed in vacuo, and the residue is purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3 g, 90.2% yield). 1HNMR (CD2Cl2): δ 7.41 (d, 1H), 7.33 (d, 1H), 2.84 (t, 2H), 2.23 (t, 2H), 1.73-1.27 (m, 28H), 0.89 (m, 6H).

Aufarbeitung

  1. customThis mixture is bubbled with nitrogen for 5 minutes
  2. customThe triethylamine is evaporated
  3. additionhexane (150 mL) is added
  4. filtrationThis mixture is filtered
  5. customto remove solid salts
  6. washThe organic layer is washed with 1M hydrochloric acid (50 mL) and brine (50 mL)
  7. dry with materialdried over MgSO4
  8. customThe solvent is removed in vacuo
  9. customthe residue is purified by chromatography on silica gel
  10. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-c4bfc79b01a74910860b7461f34e8095
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846855B2

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