Allyltributylstannane → HCID 67516102, compound

HRID 2173197Notes

Reaction equation

HRID 2173197 reaction equation
Br[C:2]1[CH:11]=[C:10]([F:12])[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[Cl-].[Li+]>C1(C)C=CC=CC=1>[CH2:15]([C:2]1[CH:11]=[C:10]([F:12])[C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1)[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 66643914HCID 66643914, compound

Product 1

HCID 67516102HCID 67516102, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask charged with 5-bromo-7-fluoro-2-benzofuran-1 (3H)-one (300 mg, 1.3 mmol) and a stir bar was added allyl tri-n-butyltin (0.6 mL, 2.0 mmol), palladium tetrakis triphenylphosphine (230 mg, 0.19 mmol), lithium chloride (170 mg, 3.9 mmol), and toluene (5 mL). The mixture was purged three times with nitrogen, and heated to reflux for 4 hours. LC showed formation of the desired product, which was purified by silica gel chromatography to deliver 5-allyl-7-fluoro-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 193 [M+1]+;

Workup

  1. customThe mixture was purged three times with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-3c266f404b654ddf84ccdc2d257cf0f5
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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