HCID 24850931, compound → 5,5'-(2,5-Bis(methylsulfinyl)-1,4-phenylene)bis(2-propylthiophene)

HRID 384244Notes

Reaction equation

HRID 384244 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([CH3:10])=[O:9])[C:5](Br)=[CH:4][C:3]=1[S:12]([CH3:14])=[O:13].[CH2:15]([C:18]1[S:19][C:20]([Sn](C)(C)C)=[CH:21][CH:22]=1)[CH2:16][CH3:17]>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>[CH3:14][S:12]([C:3]1[CH:4]=[C:5]([C:20]2[S:19][C:18]([CH2:15][CH2:16][CH3:17])=[CH:22][CH:21]=2)[C:6]([S:8]([CH3:10])=[O:9])=[CH:7][C:2]=1[C:20]1[S:19][C:18]([CH2:15][CH2:16][CH3:17])=[CH:22][CH:21]=1)=[O:13]

Participants

4

Reactant 2

HCID 24850931HCID 24850931, compoundHCID 670800382-Propyl-5-trimethylstannylthiophene

Product 1

HCID 670800625,5'-(2,5-Bis(methylsulfinyl)-1,4-phenylene)bis(2-propylthiophene)Yield 81%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

1,4-dibromo-2,5-bis(methylsulfinyl)benzene 3 (2.60 g, 7.21 mmol) was added to a solution of 2-propyl-5-trimethylstannylthiophene (5.0 g, 17.3 mmol) in anhydrous Toulene (48 mL), and the resulting mixture was purged with nitrogen for 30 min. Pd(PPh3)4 (0.833 g, 0.072 mmol) was then added, and the reaction mixture was heated to 100° C. overnight. Excess Toulene was removed under high vacuum, and the residue was dissolved in ethyl acetate and treated with 10% aqueous KF. The mixture was filtered through a pad of Celite. The filtrate was dried over Mg2SO4, filtered, and the solvent removed in vacuo. The crude product was purified by flash chromatography (silica gel, eluent:hexane/EA) 2:1) to afford 2.63 g (81%) of 2c.

Workup

  1. customthe resulting mixture was purged with nitrogen for 30 min
  2. customExcess Toulene was removed under high vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. additiontreated with 10% aqueous KF
  5. filtrationThe mixture was filtered through a pad of Celite
  6. dry with materialThe filtrate was dried over Mg2SO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe crude product was purified by flash chromatography (silica gel, eluent:hexane/EA) 2:1)

Sources & evidence

ORD record
ord-16b42de9b3e74583a341fbf11674830d
Source dataset
uspto-grants-2013_02
Patent number
US08367717B2

Reaction notes

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