Allyltributylstannane → HCID 67516453, compound

HRID 1465778Notes

Reaction equation

HRID 1465778 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[Cl:12].[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]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[C:3]=1[Cl:12])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 67518202HCID 67518202, compound

Product 1

HCID 67516453HCID 67516453, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask charged with 5-bromo-4-chloro-2-benzofuran-1(3H)-one (190 mg, 0.77 mmol) and a stir bar was added allyl tri-n-butyltin (0.36 mL, 1.2 mmol), PdCl2(dppf)-DCM complex, lithium chloride (0.098 mg, 2.3 mmol), and toluene (5 mL). The flask was fitted with a condensor, purged three times with nitrogen, and heated to reflux for 6 hours. When LC showed complete reaction, the crude material was purified by MPLC to provide 5-allyl-4-chloro-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 209 [M+1]+;

Workup

  1. customThe flask was fitted with a condensor
  2. custompurged three times with nitrogen
  3. temperatureheated
  4. temperatureto reflux for 6 hours
  5. customreaction
  6. customthe crude material was purified by MPLC

Sources & evidence

ORD record
ord-2e94240cc32841338724d7afb42efedf
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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