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

HRID 1175103Notes

Reaction equation

HRID 1175103 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 669248432-Dec-1-ynyl-3-decanyldithieno[2,3-d:2',3'-d']thieno [3,2-b:4,5-b']dithiopheneYield 90.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
130 °C

Procedure

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) was 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 was bubbled with nitrogen for 5 minutes and then heated up to 130° C. under argon for 16 hours. The triethylamine was evaporated and hexane (150 mL) was added. This mixture was filtered to remove solid salts. The organic layer was washed with 1 M hydrochloric acid (50 mL) and brine (50 mL), then dried over MgSO4. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel eluted with hexane to produce the target compound (2.3 g, 90.2%). 1H NMR: Solvent 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).

Workup

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

Sources & evidence

ORD record
ord-0d48e5dd01034b379a4dafb3442841cd
Source dataset
uspto-grants-2010_11
Patent number
US07838623B2

Reaction notes

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