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

HRID 1260263노트

반응식

HRID 1260263 반응식
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]

참가 물질

5

반응물 2

HCID 81998TributylvinyltinHCID 117464905-Bromo-2-nitroanisole

생성물 1

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

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-357bb11301a746f995a6e8ac447ef29b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470810B2

반응 노트

불러오는 중…