Tributylvinyltin → 2-Methoxy-1-nitro-4-vinylbenzene

HRID 1260263Notes

Reaction equation

HRID 1260263 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([CH:13]=[CH2:14])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 117464905-Bromo-2-nitroanisole

Product 1

HCID 536287222-Methoxy-1-nitro-4-vinylbenzeneYield 355.5%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 1140TolueneSolvent

Procedure

4-Bromo-2-methoxy-1-nitro-benzene (691 mg, 3.14 mmol), tributyl-vinyl-stannane (1.2 g, 3.77 mmol), triphenylphospine (49 mg, 0.19 mmol) and tetrakistriphenylphosphinpalladium(0) (73 mg, 0.06 mmol) were dissolved in toluene (25 ml) and stirred for 5 hours at reflux. The reaction mixture was concentrated in vacuo. The residue was partitioned between water (25 ml) and diethyl ether (50 ml). The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to yield an oil (2.0 g). The residue was purified via silica gel chromatography with cyclohexane/ethyl acetate (gradient 0-25%). Fractions containing the product were combined, the solvent evaporated to give an oil (435 mg, 72%).

Workup

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between water (25 ml) and diethyl ether (50 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-357bb11301a746f995a6e8ac447ef29b
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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