2,5-dibromo-3,4-dimethylthieno[2,3-b]thiophene → HCID 23070268, compound

HRID 351298Notes

Reaction equation

HRID 351298 reaction equation
Br[C:2]1[S:11][C:5]2[S:6][C:7](Br)=[C:8]([CH3:9])[C:4]=2[C:3]=1[CH3:12].B([O-])[O-].[CH2:16]([C:22]1[CH:23]=[CH:24][S:25][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Na+].[Na+].[Na]>COCCOC.C(OCC)C>[CH2:16]([C:22]1[CH:23]=[C:24]([C:2]2[S:11][C:5]3[S:6][C:7]([C:24]4[S:25][CH:26]=[C:22]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:23]=4)=[C:8]([CH3:9])[C:4]=3[C:3]=2[CH3:12])[S:25][CH:26]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 28201622,5-dibromo-3,4-dimethylthieno[2,3-b]thiopheneHCID 5360545SodiumHCID 178442413HCID 178442413, compound

Product 1

HCID 23070268HCID 23070268, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2,5-dibromo-3,4-dimethylthieno[2,3-b]thiophene (3.02 g, 9.28 mmol) and sodium 4-hexylthiophene boronate (5.14 g, 20.4 mmol) in degassed DME (200 ml) was added tetrakis(triphenyl-phosphine)palladium(0) (0.5 g, 5 mol %). The solution was heated to reflux and a saturated solution of sodium hyodrogen carbonate (4.2 g, 49 mmol) was added slowly. The reaction was refluxed for 16 h, cooled and diluted with diethyl ether. The layers were separated and the organics washed with 5% HCl, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography over silica (eluent: petrol) to afford the product after recrystallisation from petroi (1.03 g, 22%). :M/Z 500 (M+). Found C, 66.9.1, H, 6.9, S, 25.3. Calc. for C28H36S4 C, 67.2; H 7.2, S, 25.6. NMR gave the expected signals.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureThe reaction was refluxed for 16 h
  4. temperaturecooled
  5. customThe layers were separated
  6. washthe organics washed with 5% HCl, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified by column chromatography over silica (eluent: petrol)
  11. customto afford the product
  12. customafter recrystallisation from petroi (1.03 g, 22%)
  13. customNMR gave the expected signals

Sources & evidence

ORD record
ord-cc216c3dd21040b7992e4494986f7e52
Source dataset
uspto-grants-2007_02
Patent number
US07183418B2

Reaction notes

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