2-Bromo-6-methoxynaphthalene → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene

HRID 1582889노트

반응식

HRID 1582889 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.C[Sn](C)(C)[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]2[O:25][CH2:26][O:27][C:18]=2[CH:17]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:26]1[O:27][C:18]2[C:19](=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]4)[CH:17]=2)[O:25]1

참가 물질

5

반응물 2

HCID 787862-Bromo-6-methoxynaphthaleneHCID 10782610Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane

생성물 1

HCID 227164436-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene수율 71%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

Tetrakis(triphenylphosphine)palladium (0) (120 mg) and cuprous bromide (20 mg) were added to a solution of 2-bromo-6-methoxynaphthalene (0.3 g, 1.27 mmol) and trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane, 62, (0.45 g, 1.37 mmol) in THF (30 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 for 16 h. After cooling, THF was evaporated and 50 mL ethyl acetate was added to the residue. The solution was washed with water. The organic layer was separated and passed through a Celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4), and evaporated in vacuo. The residue was chromatographed using a 80:20 mixture of hexanes:ethyl acetate to give the desired product 45 (0.29 g) in 71% yield; mp 165-167° C.; IR (KBr) 2911, 1609, 1520, 1482, 1429, 1393, 1344, 1257, 1199 cm−1; 1H NMR (CDCl3) δ3.94 (3H, s), 6.14 (2H, s), 6.88 (1H, s), 7.16-7.21 (2H, m), 7.31 (1H, dd, J1=8.5, J2=1.9), 7.47 (1H, s), 7.67-7.77 (3H, m); 13C NMR δ55.89, 103.45, 105.92, 106.19, 111.69, 119.86, 126.90, 127.02, 127.55, 129.23, 130.09, 133.76, 133.85, 134.48, 143.38, 147.52, 151.47, 158.62; HRMS (EI) calcd for C18H13NO5 m/z: 323.0794; found: 323.0788.

후처리

  1. temperatureThe mixture was then refluxed under N2 for 16 h
  2. temperatureAfter cooling
  3. customTHF was evaporated
  4. addition50 mL ethyl acetate was added to the residue
  5. washThe solution was washed with water
  6. customThe organic layer was separated
  7. customto remove
  8. washThe organic layer was then washed with brine
  9. dry with materialdried (anhydrous Na2SO4)
  10. customevaporated in vacuo
  11. customThe residue was chromatographed
  12. additiona 80:20 mixture of hexanes

출처 및 근거

ORD 기록
ord-5fb11b969d0f43d9adde46764d108fec
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06740650B2

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