Tributylvinyltin → HCID 22730560, compound

HRID 2085776Notes

Reaction equation

HRID 2085776 reaction equation
Br[C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH:13]([Sn](CCCC)(CCCC)CCCC)=[CH2:14].O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN1C(=O)CCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:9]1[CH:10]=[CH:11][C:4]2[S:3][C:2]([CH:13]=[CH2:14])=[C:6]([CH3:7])[C:5]=2[CH:8]=1

Participants

6

Reactant 3

HCID 81998TributylvinyltinHCID 521585Tris(furan-2-yl)phosphaneHCID 27355482-Bromo-5-chloro-3-methylbenzo[b]thiophene

Product 1

HCID 22730560HCID 22730560, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-bromo-5-chloro-3-methylbenzthiophene (5 g, 19.1 mmol), vinyltributylstannane (5.59 mL, 19.1 mmol), Pd2dba3 (525 mg, 0.57 mmol), and tri(2-furyl)phosphine (532 mg, 2.29 mmol) in NMP (70 mL) at 90° C. was stirred for 18 hours and concentrated. The concentrate was purified by flash column chromatography on silica gel with hexanes to provide the desired product. MS (ESI(−)) m/e 207 (M−H)−.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with hexanes

Sources & evidence

ORD record
ord-0a6b06b7480448d6bf111fa14b1acda7
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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