2-(Tri-n-butylstannyl)thiophene → HCID 67042477, compound

HRID 468709Notes

Reaction equation

HRID 468709 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9](Br)=[C:10]([C:12]([O:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH:11]=2)=[CH:4][C:3]=1[C:28]([O:30][CH2:31][CH:32]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:29].C([Sn](CCCC)(CCCC)[C:48]1[S:49][CH:50]=[CH:51][CH:52]=1)CCC>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.CN(C=O)C>[S:6]1[CH:2]=[CH:3][CH:4]=[C:5]1[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([C:50]3[S:49][CH:48]=[CH:52][CH:51]=3)=[C:10]([C:12]([O:14][CH2:15][CH:16]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:13])[CH:11]=2)=[CH:4][C:3]=1[C:28]([O:30][CH2:31][CH:32]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[O:29]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 67042476HCID 67042476, compound

Product 1

HCID 67042477HCID 67042477, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To the mixture of bis(2-butyl-1-octyl) 5,5′-dibromo-2,2′-bithiophene-4,4′-dicarboxylate (1.00 g, 1.34 mmol) and 2-tributylstannylthiophene (1.50 g, 4 mmol) was added Pd(PPh3)4 (46 mg, 0.04 mmol), and anhydrous DMF (15 ml). The mixture was placed under vacuum and flushed with argon several times and was put on a microwave reactor with a setting of 160° C. for 60 min. The reaction mixture was cooled to room temperature and the solvent was removed. The residue was washed with methanol to remove traces of DMF. After drying, the liquid was dissolved in hexane and purified twice by column chromatography on silica gel using a mixture of hexane/ethyl acetate (9/1) (Rf=0.5). A light yellow liquid was obtained. Yield: 1.01 g (100%).

Workup

  1. customflushed with argon several times
  2. customthe solvent was removed
  3. washThe residue was washed with methanol
  4. customto remove traces of DMF
  5. customAfter drying
  6. dissolutionthe liquid was dissolved in hexane
  7. custompurified twice by column chromatography on silica gel using
  8. additiona mixture of hexane/ethyl acetate (9/1) (Rf=0.5)
  9. customA light yellow liquid was obtained

Sources & evidence

ORD record
ord-6bd8741ed46b48b491daf06457267eba
Source dataset
uspto-grants-2014_01
Patent number
US08624232B2

Reaction notes

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