Allyltributylstannane → 5-Allyl-2,1,3-benzoxadiazole

HRID 1519502Notes

Reaction equation

HRID 1519502 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.[Cl-].[Li+].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.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>[CH2:15]([C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 27762985-Bromo-2,1,3-benzoxadiazole

Product 1

HCID 595687145-Allyl-2,1,3-benzoxadiazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 ml) and added Lithium chloride (6.4 g, 150 mmol), Pd(Ph3P)4 (2.90 g, 2.50 mmol), and allyl tributyltin (19 ml, 60 mmol). The reaction mixture was degassed and refluxed under N2 for 3 hrs. It was cooled and poured into water then extracted with ethyl acetate. The organic layer was washed with brine 1×, dried and evaporated to dryness. The residue was chromatographed through 120 g ISCO Redi-Sep columns and eluted with 0-10% ethyl acetate/hexane to yield 5-allyl-2,1,3-benzoxadiazole.

Workup

  1. customThe reaction mixture was degassed
  2. temperaturerefluxed under N2 for 3 hrs
  3. temperatureIt was cooled
  4. additionpoured into water
  5. extractionthen extracted with ethyl acetate
  6. washThe organic layer was washed with brine 1×
  7. customdried
  8. customevaporated to dryness
  9. customThe residue was chromatographed through 120 g ISCO Redi-Sep columns
  10. washeluted with 0-10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3474310f6c5840c889791effad8459ca
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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