Potassium Carbonate → HCID 72326549, compound

HRID 1176967Notes

Reaction equation

HRID 1176967 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[C:19]([O-:22])([O-])=O.[K+].[K+].[Li+].[Cl-].[CH2:27]([O:39][C:40]1[CH:45]=[CH:44][C:43]([CH:46]=[CH2:47])=[CH:42][C:41]=1[O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH2:49]([O:48][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:47]=[CH:46][C:43]4[CH:44]=[CH:45][C:40]([O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[C:41]([O:22][CH2:19][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH3:49])[CH:42]=4)=[CH:14][CH:13]=3)=[O:11])=[CH:4][CH:3]=2)[CH:44]=[CH:45][C:40]=1[O:39][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 964304,4'-DibromobenzilHCID 433294Lithium ChlorideHCID 59560832HCID 59560832, compound

Product 1

HCID 72326549HCID 72326549, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A Schlenk tube was charged with 4,4′-dibromobenzil (1.8 g, 4.9 mmol), K2CO3 (3.38 g, 24.5 mmol), Bu4NBr (1.58 g, 4.9 mmol), LiCl (0.21 g, 4.9 mmol), Pd(OAc)2 (0.11 g, 0.49 mmol), 1,2-bis-dodecyloxy-4-vinyl-benzene (JYC-II-004-A) (5.78 g, 12.2 mmol), and 40 mL of dry DMF. The reaction mixture was heated at 100° C. under Ar over the weekend. The reaction mixture was allowed to cool down to room temperature and extracted with CH2Cl2. The organic phase was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), dichloromethane:hexanes=1:1 (v/v)), then dichloromethane:hexanes=3:2 (v/v)) to give a bright yellow solid. The solid was further recrystallized from CH2Cl2/hexanes to give a bright yellow solid (4.27 g, 75.6%).

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), dichloromethane:hexanes=1:1 (v/v))
  7. customdichloromethane:hexanes=3:2 (v/v)) to give a bright yellow solid
  8. customThe solid was further recrystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-e20a54ff28364db7b40e488c40ecf21a
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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