(5-Hexylthiophen-2-yl)trimethylstannane → HCID 67079691, compound

HRID 384241Notes

Reaction equation

HRID 384241 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:21]1[S:25][C:24]([Sn](C)(C)C)=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)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>[CH3:14][S:12]([C:3]1[CH:4]=[C:5]([C:24]2[S:25][C:21]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:22][CH:23]=2)[C:6]([S:8]([CH3:10])=[O:9])=[CH:7][C:2]=1[C:24]1[S:25][C:21]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:22][CH:23]=1)=[O:13]

Participants

5

Reactant 2

HCID 11267529(5-Hexylthiophen-2-yl)trimethylstannaneHCID 24850931HCID 24850931, compound

Product 1

HCID 67079691HCID 67079691, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1,4-dibromo-2,5-bis(methylsulfinyl)benzene 3 (0.900 g, 2.5 mmol) was added to a solution of 4b (1.82 g, 5.5 mmol) in anhydrous DMF (30 mL), and the resulting mixture was purged with Ar for 30 min. Pd(PPh3)4 (87 mg, 0.075 mmol) was then added, and the reaction mixture was heated to 80° C. overnight. Excess DMF 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/THF) 1:1) to afford 1 g (75%) of 2b.

Workup

  1. customthe resulting mixture was purged with Ar for 30 min
  2. customExcess DMF 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/THF) 1:1)

Sources & evidence

ORD record
ord-722a0876ad0d4ebfb9ad5fd84a41da11
Source dataset
uspto-grants-2013_02
Patent number
US08367717B2

Reaction notes

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