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

HRID 1519517Notes

Reaction equation

HRID 1519517 reaction equation
[Cl-].[Li+].Br[C:4]1[CH:12]=[CH:11][C:7]2=[N:8][O:9][N:10]=[C:6]2[CH:5]=1.[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:4]1[CH:12]=[CH:11][C:7]2=[N:8][O:9][N:10]=[C:6]2[CH:5]=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

Lithium chloride (0.64 g, 15.1 mmol) was added to a mixture of 5-bromo-2,1,3-benzoxadiazole (1.0 g, 5.0 mmol), tetrakis(triphenylphosphine)palladium (0.29 g, 0.25 mmol) and allyl tri-n-butyltin (1.87 ml, 6.0 mmol) in 30 ml toluene then refluxed for 3 hours. The reaction was filtered, concentrated, and loaded into an ISCO 120 gm Redi-Sep then eluted with a gradient of 0-50% ethyl acetate/hexane. 1H-NMR (500 MHz, CDCl3) δ ppm 7.76 (d, J=9 Hz, 1H), 7.59 (s, 1H), 7.28 (d, J=9 Hz, 1H), 5.95-6.03 (m, 1H), 5.24 (d, J=10 Hz, 1H), 5.20 (d, J=15 Hz, 1H), 3.49 (d, J=6.5 Hz, 2H).

Workup

  1. temperaturethen refluxed for 3 hours
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. washthen eluted with a gradient of 0-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-defba728c9df41128994d81f7b017c15
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…