Trifluoroacetic acid → HCID 57470088, compound

HRID 1260258Notes

Reaction equation

HRID 1260258 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].FC(F)(F)C(O)=O.[CH2:20]([N:27]([CH2:33]OC)[CH2:28][Si](C)(C)C)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl.C(OCC)(=O)C>[CH2:20]([N:27]1[CH2:33][CH2:9][CH:8]([C:6]2[CH:5]=[CH:4][C:3]([N+:10]([O-:12])=[O:11])=[C:2]([F:1])[CH:7]=2)[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2×HCID 117895864-Ethenyl-2-fluoro-1-nitrobenzene

Product 1

HCID 57470088HCID 57470088, compoundYield 139.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Fluoro-1-nitro-4-vinyl-benzene (360 mg, 2.15 mmol) was dissolved in dichloromethane (2 ml), trifluoroacetic acid (70 μl, 0.88 mmol) was added, followed by slow addition of N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (633 mg, 2.67 mmol). Stirring was continued for 2 h at room temperature. Another portion of N-benzyl-N(methoxymethyl)-N-trimethylsilylmethylamine (300 mg, 1.26 mmol) was added and stirring continued for another 30 minutes. The reaction mixture was diluted with ethyl acetate (25 ml), washed with aqueous NaHCO3 (15 ml). The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield an oil (900 mg). The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (gradient 0-25%). Fractions containing the product were combined, the solvent evaporated to yield an oil (550 mg, 85%).

Workup

  1. stirringstirring
  2. waitcontinued for another 30 minutes
  3. washwashed with aqueous NaHCO3 (15 ml)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0d81cedb2419466a90588ff58d46aaa4
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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