Dimethylformamide → 4,4'-(Bicyclo[2.2.1]heptane-2,5-diyl)bis(2-methylphenol)

HRID 40444

반응식

HRID 40444 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]12[CH2:16][C:13]([CH2:14][CH2:15]1)=[CH:12][CH:11]=2.CN([CH:20]=[O:21])C.C(N([CH2:27][CH3:28])CC)C>C(OCC)(=O)C.C(O)=O>[CH:10]12[CH2:16][CH:13]([CH:14]([C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=3)[CH2:15]1)[CH2:12][CH:11]2[C:2]1[CH:3]=[CH:4][C:20]([OH:21])=[C:27]([CH3:28])[CH:7]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 168964-Bromo-2-methylphenolHCID 18006658Norborna-diene

생성물 1

HCID 676059444,4'-(Bicyclo[2.2.1]heptane-2,5-diyl)bis(2-methylphenol)수율 43%

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

4-Bromo-2-methylphenol (2.03 grams, 10.8 mmol), (tris-o-tolylphosphine)2PdCl2 (0.0422 gram, 0.0537 mmol), and norbornadiene (0.257 gram, 2.79 mmol) were charged to an appropriately sized and equipped reaction vessel under nitrogen. DMF (36 mL), triethylamine and formic acid were added to what was observed to be a yellow suspension. The mixture was then heated to 75° C. in an oil bath. Upon such heating, the reaction mixture became a yellow solution, black particles appeared and a very slow evolution of gas was observed. The reaction mixture was stirred overnight at this temperature. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was separated and dried over anhydrous MgSO4. PP308-2, 5, (4,4′-(Bicyclo[2.2.1]heptane-2,5-diyl)bis(2-methylphenol)) was confirmed by GC-MS of the crude product (43% yield).

후처리

  1. customequipped
  2. customreaction vessel under nitrogen
  3. temperatureAfter cooling
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4

출처 및 근거

ORD 기록
ord-f91b90d3c80848908aaec333c56a1375
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530133B2

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