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Tributylvinyltin → N-(2-benzoyl-4-vinylphenyl)-2,2,2-trifluoro-acetamide

HRID 2053424
Notes
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Reaction equation

HRID 2053424 reaction equation
[C:1]([C:9]1[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([Sn](CCCC)(CCCC)C=C)[CH2:24]CC>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:9]1[CH:14]=[C:13]([CH:23]=[CH2:24])[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 4702292N-(2-benzoyl-4-bromophenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 59655009N-(2-benzoyl-4-vinylphenyl)-2,2,2-trifluoro-acetamideYield 70%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst
HCID 1140
Toluene
Solvent
2×

Procedure

To a solution of N-(2-benzoyl-4-bromophenyl)-2,2,2-trifluoroacetamide (a) (0.37 g, 1.0 mmol) in degassed dry toluene (10 mL) was added a solution of tetrakis(triphenyl-phosphine) palladium [Pd(PPh3)4] in toluene (5 mL) under argon. The mixture was heated to reflux and tributyl(vinyl)tin (0.29 mL, Immol) was added in a dropwise fashion. After refluxing overnight, the mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel [hexanes: ethyl acetate (9:1)] to give N-(2-benzoyl-4-vinylphenyl)-2,2,2-trifluoro-acetamide (b) (0.22 g, 70%). 1H NMR (300 MHz, CDCl3) δ 12.0 (s, 1H), 8.62 (d, J=10.9 Hz, 1H), 7.80-7.60 (m, 5H), 7.60-7.43 (m, 2H), 6.65 (dd, J=11, 19.6 Hz, 1H), 5.69 (d, J=19.6 Hz, 1H), 5.29 (d, J=11 Hz,1H). MS: 320.2 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter refluxing overnight
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel [hexanes: ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-65932af4dbd54c528fb0a9285d7da086
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07326788B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes