Toluene → HCID 71065165, compound

HRID 1522718Notes

Reaction equation

HRID 1522718 reaction equation
[C:1]1([C:7]2[C:8](=[O:32])[C:9]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:10]([C:19]3[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:39]1([CH3:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:7]2[C:8](=[O:32])[C:9]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:10]([C:19]3[CH:24]=[CH:23][C:22]([C:41]4[CH:42]=[CH:43][C:44]5[C:16]6[C:15](=[CH:14][CH:13]=[CH:12][CH:17]=6)[C:45]([CH2:21][CH2:22][CH3:23])([CH2:10][CH2:9][CH3:26])[C:39]=5[CH:40]=4)=[CH:21][CH:20]=3)[C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([C:41]3[CH:42]=[CH:43][C:44]4[C:6]5[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=5)[C:45]([CH2:8][CH2:7][CH3:11])([CH2:24][CH2:19][CH3:20])[C:39]=4[CH:40]=3)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 31068682,5-Diphenyl-3,4-di(4-bromophenyl)cyclopentadienone

Product 1

HCID 71065165HCID 71065165, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

Tetrakis(triphenylphosphine)-palladium (0) (1.48 g, 1.3 mmol) was added to a solution of (9) (13.8 g, 26 mmol) and (8) (22.6 g, 77 mmol) in a mixture of ethanol (100 mL), 2M aqueous sodium carbonate (100 mL) and toluene (300 mL) that had been deoxygenated with argon. The solution was deoxygenated and heated at reflux for 16 hours, then poured into methanol. The resulting brown precipitate was filtered, dissolved in chloroform, washed with brine, and dried over magnesium sulfate. The solution was poured into methanol, and the brown precipitate filtered to give (10) (22.4 g, 99%).

Workup

  1. customhad been deoxygenated with argon
  2. customThe solution was deoxygenated
  3. temperatureheated
  4. temperatureat reflux for 16 hours
  5. additionpoured into methanol
  6. filtrationThe resulting brown precipitate was filtered
  7. dissolutiondissolved in chloroform
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. additionThe solution was poured into methanol
  11. filtrationthe brown precipitate filtered

Sources & evidence

ORD record
ord-32b1ce94186c4c4eb2346c62dbee6887
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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