Sodium Carbonate → HCID 68018442, compound

HRID 1049670Notes

Reaction equation

HRID 1049670 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, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

25 g (60.5 mmol) of (3-bromophenyl)[1,1′;3′,1″]-terphenyl-5′-ylmethanone and 9 g (60.5 mmol) of styreneboronic acid [2156-04-9] are dissolved in 300 ml of toluene, and 100 ml of a 2 M sodium carbonate solution are added. The reaction mixture is carefully degassed, 200 mg of tetrakistriphenylphosphinepalladium are added, and the mixture is heated under reflux for 20 h. The solution is cooled to room temperature, and 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. The residue is recrystallised from heptane/acetonitrile 1:1, giving 12 g (27 mmol) (45%) of a white solid having a purity of 99.9%.

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 h
  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
  10. customThe residue is recrystallised from heptane/acetonitrile 1:1

Sources & evidence

ORD record
ord-3ee77c4bd13a4128a584bbd6e93d245c
Source dataset
uspto-grants-2016_07
Patent number
US09382253B2

Reaction notes

Loading…