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

HRID 1260263ノート

反応式

HRID 1260263 の反応式
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]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 117464905-Bromo-2-nitroanisole

生成物 1

HCID 536287222-Methoxy-1-nitro-4-vinylbenzene収率 355.5%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-357bb11301a746f995a6e8ac447ef29b
出典データセット
uspto-grants-2013_06
特許番号
US08470810B2

反応ノート

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