HCID 22467461, compound → HCID 22467621, compound

HRID 1934730Notes

Reaction equation

HRID 1934730 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=1)=[O:8].[CH2:22](C([Sn])=C(CCCC)CCCC)[CH2:23]CC>C1(C)C=CC=CC=1.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>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]2[CH:20]=[C:2]([CH:22]=[CH2:23])[CH:3]=[CH:4][C:5]=2[F:21])=[CH:12][C:13]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 22467461HCID 22467461, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 22467621HCID 22467621, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-bromo-N-(4-chloro-3-methoxybenzyl)-2-fluorobenzamide (2.00 g) in toluene (40 mL) were added tetrakis(triphenylphosphine)palladium (217 mg) and tributylvinyltin (1.87 g), and the mixture was heated for 4 hours under reflux. After evaporation of the solvent, the residue was partitioned between ethyl acetate and saturated potassium fluoride solution. The remaining precipitates were removed by filtration. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (3:1) to give N-(4-chloro-3-methoxybenzyl)-2-fluoro-5-vinylbenzamide as pale yellow powders (1.51 g).

Workup

  1. temperaturethe mixture was heated for 4 hours
  2. temperatureunder reflux
  3. customAfter evaporation of the solvent
  4. customthe residue was partitioned between ethyl acetate and saturated potassium fluoride solution
  5. customThe remaining precipitates
  6. customwere removed by filtration
  7. washThe separated organic layer was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by a silica gel column chromatography
  11. washeluting with a mixture of hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-5c132a0d2f914238a520a8dfb7be682d
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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