Tributylvinyltin → N-(4-chloro-2-vinyl-phenyl)-acetamide

HRID 2220206Notes

Reaction equation

HRID 2220206 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:12])[CH3:11].[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10](=[O:12])[CH3:11])=[C:2]([CH:13]=[CH2:14])[CH:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 282685N-(2-bromo-4-chlorophenyl)acetamide

Product 1

HCID 59717611N-(4-chloro-2-vinyl-phenyl)-acetamideYield 64%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of N-(2-bromo-4-chloro-phenyl)-acetamide (2 g, 8 mmol) in toluene (20 mL) was added tributyl(vinyl)tin (3.05 mL, 10.5 mmol) and dichlorobis(triphenylphosphine)palladium (II) (1.41 g, 2 mmol). The reaction mixture was heated at 95° C. for 1 hour, and the solvent removed in vacuo. The residue obtained was purified by flash chromatography eluting with 20% ethyl acetate/CH2Cl2 to give N-(4-Chloro-2-vinyl-phenyl)-acetamide (1 g, 64%). HPLC: Rt=2.16 min. m/z=196 (M+H+).

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue obtained
  3. customwas purified by flash chromatography
  4. washeluting with 20% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-c7e0da0fa4614e29a3c285ba073b6a82
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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