Cesium carbonate → HCID 58526509, compound

HRID 1190243Notes

Reaction equation

HRID 1190243 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[N:28]=[C:27]([C:29]3[CH:30]=[C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:32]=[C:33]([Cl:35])[CH:34]=3)[N:26]=[C:25]([C:42]3[CH:47]=[C:46](Br)[CH:45]=[C:44](Br)[CH:43]=3)[N:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([C:23]2[N:28]=[C:27]([C:29]3[CH:30]=[C:31]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:32]=[C:33]([Cl:35])[CH:34]=3)[N:26]=[C:25]([C:42]3[CH:47]=[C:46]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:45]=[C:44]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:43]=3)[N:24]=2)[CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 58526512HCID 58526512, compound

Product 1

HCID 58526509HCID 58526509, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, phenylboronic acid (904 mg), 4,6-bis(5-chlorobiphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine (1.70 g), cesium carbonate (2.41 g) and tetrakis(triphenylphosphine)palladium (114 mg) were suspended in tetrahydrofuran (80 mL), and the mixture was refluxed for 18 hours. The reaction mixture was left to stand at room temperature, and then low-boiling ingredients were distilled away under a reduced pressure. Methanol was added to the reaction mixture, and the solid precipitate was recovered by filtration, and purified by silica gel chromatography using a chloroform/hexane (1:2 to 1:0) mixed liquid as a developing solvent to give 1.42 g of the target 2,4-bis(5-chlorobiphenyl-3-yl)-6-[(1,1′:3′,1″)-terphenyl-5′-yl]-1,3,5-triazine as a yellowish white powder (yield: 84%).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. waitThe reaction mixture was left
  3. customto stand at room temperature
  4. distillationlow-boiling ingredients were distilled away under a reduced pressure
  5. additionMethanol was added to the reaction mixture
  6. filtrationthe solid precipitate was recovered by filtration
  7. custompurified by silica gel chromatography
  8. additionmixed liquid as a developing solvent

Sources & evidence

ORD record
ord-b07acd08840e417aacec9ce5a6a1d20c
Source dataset
uspto-grants-2014_03
Patent number
US08674091B2

Reaction notes

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