Sodium Carbonate → HCID 68018442, compound

HRID 590899Notes

Reaction equation

HRID 590899 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH:28](B(O)O)=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH:29]([C:30]1[CH:35]=[CH:34][C:33]([C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([C:8]([C:10]3[CH:11]=[C:12]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:13]=[C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:15]=3)=[O:9])[CH:5]=2)=[CH:32][CH:31]=1)=[CH2:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343812-Phenylvinylboronic acidHCID 68088310HCID 68088310, compound

Product 1

HCID 68018442HCID 68018442, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g of (3-bromophenyl)-[1,1′;3′,1″]terphenyl-5′-ylmethanone and 8 g of styreneboronic acid [2156-04-9] are dissolved in 300 ml of toluene, and 100 ml of a 2M sodium carbonate solution are added. The reaction mixture is carefully degassed, and 200 mg of tetrakistriphenylphosphinepalladium are added, and the mixture is heated under reflux for 20 hours. The solution is cooled to room temperature. The phases are separated. The aqueous phase is extracted three times with toluene, the combined organic phases are subsequently washed twice with water, dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo.

Workup

  1. customThe reaction mixture is carefully degassed
  2. addition200 mg of tetrakistriphenylphosphinepalladium are added
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 20 hours
  5. customThe phases are separated
  6. extractionThe aqueous phase is extracted three times with toluene
  7. washthe combined organic phases are subsequently washed twice with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-6035f4352ccd4c1f99a3b78a7bdab6a7
Source dataset
uspto-grants-2016_01
Patent number
US09236571B2

Reaction notes

Loading…