Stannane, tributyl(1-ethoxyethenyl)- → HCID 59672539, compound

HRID 1844705Notes

Reaction equation

HRID 1844705 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]([O:20]CC)=[CH2:19])CCC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:12][C:4]1[CH:3]=[C:2]([C:18](=[O:20])[CH3:19])[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 27611701,3-dibromo-5-tert-butylbenzene

Product 1

HCID 59672539HCID 59672539, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1,3-dibromo-5-(tert-butyl)benzene (664 mg, 2.22 mmol) in toluene (15 mL) were added tri-n-butyl-1-ethoxyvinyl tin (965 mg, 2.66 mmol) and Pd(PPh3)2Cl2 (150 mg 0.22 mmol) under N2. The mixture was stirred at 95° C. for 3 h, evaporated, diluted with 1,4-dioxane and 2N HCl, stirred rapidly at 25° C. for 1 h and then extracted with EA. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified by CC to afford compound P49a (310 mg, 55%).

Workup

  1. customevaporated
  2. additiondiluted with 1,4-dioxane and 2N HCl
  3. stirringstirred rapidly at 25° C. for 1 h
  4. extractionextracted with EA
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by CC
  9. customto afford compound P49a (310 mg, 55%)

Sources & evidence

ORD record
ord-3a8e61514f0b43ca8a52a8b81ff2c57b
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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