Allyltributylstannane → HCID 67515767, compound

HRID 2173186Notes

Reaction equation

HRID 2173186 reaction equation
[Br:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1Br.[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:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[Br:1])[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 66819934HCID 66819934, compound

Product 1

HCID 67515767HCID 67515767, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a flask charged with 4,5-dibromo-2-benzofuran-1(3H)-one (170 mg, 0.59 mmol) and a stir bar was added allyl tri-n-butyltin (0.18 mL, 0.59 mmol), palladium tetrakis (68 mg, 0.059 mmol), lithium chloride (50 mg, 1.2 mmol), and toluene (5 mL). The mixture was sealed with a condensor, purged three times with nitrogen, and heated to reflux for 16 hours. The reaction was diluted with EtOAc (50 mL), adsorbed onto silica gel, and purified by silica gel flash chromatography to afford 5-allyl-4-bromo-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 253 [M+1]+;

Workup

  1. customThe mixture was sealed with a condensor
  2. custompurged three times with nitrogen
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. additionThe reaction was diluted with EtOAc (50 mL)
  6. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-2f3e6a67db8f422f8e120a088f701d42
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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