Tri(butyl)vinyltin → Tert-butyl 2-(benzamido)-4-vinylbenzoate

HRID 1673344Notes

Reaction equation

HRID 1673344 reaction equation
[C:1]([NH:9][C:10]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:24](C([Sn])=C(CCCC)CCCC)[CH2:25]CC>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>[C:1]([NH:9][C:10]1[CH:22]=[C:21]([CH:24]=[CH2:25])[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 53438229Tri(butyl)vinyltinHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Product 1

HCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoateYield 46.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.54 g of tetrakis(triphenylphosphine)palladium (0) was added to 35 mL of toluene solution containing 3.5 g of tert-butyl 2-(benzamido)-4-bromobenzoate and 5.0 g of tributylvinyl tin, and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane; ethyl acetate=20:1] to obtain 1.4 g of tert-butyl 2-(benzamido)-4-vinylbenzoate as white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 2 hours
  3. custominsoluble were removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane; ethyl acetate=20:1]

Sources & evidence

ORD record
ord-dbe537576a7d4f66886e7bc244baa9f4
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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