Allyltributylstannane → HCID 67516513, compound

HRID 2173194Notes

Reaction equation

HRID 2173194 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[F:12].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15].[Cl-].[Li+]>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.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[F:12])[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 666440385-Bromo-4-fluoro-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 67516513HCID 67516513, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a flask charged with 5-bromo-4-fluoro-2-benzofuran-1(3H)-one (52 mg, 0.22 mmol) and a stir bar was added allyl tri-n-butyltin (0.10 mL, 0.34 mmol), palladium tetrakis (39 mg, 0.034 mmol), lithium chloride (29 mg, 0.68 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-4-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-ed9399ee40a64d26bc52152b34eb3162
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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