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

HRID 40444

反応式

HRID 40444 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f91b90d3c80848908aaec333c56a1375
出典データセット
uspto-grants-2013_09
特許番号
US08530133B2

関連ノート

読み込み中…