Sodium Carbonate → HCID 22138030, compound

HRID 1827618Notes

Reaction equation

HRID 1827618 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][C:9]2[CH:14]=[C:13]([Br:15])[CH:12]=[C:11](Br)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]1(B(O)O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][C:9]2[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25][CH:24]=3)[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 221380311-(2,2-Diphenylvinyl)-3,5-dibromobenzene

Product 1

HCID 22138030HCID 22138030, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under an atmosphere of argon, 1-(2,2-diphenylvinyl)-3,5-dibromobenzene (8.3 g, 20 mmole), 1-naphthaleneboronic acid (3.4 g, 20 mmole) and tetrakis(triphenylphosphine)palladium(0) (0.46 g, 0.4 mmole, 2% Pd) were dissolved into toluene (50 ml). To the obtained solution, a 2 M aqueous solution of sodium carbonate (30 ml, 60 mmole, 3 eq) was added. The resultant solution was heated under refluxing for 10 hours and left standing for one night. The formed organic layer was separated, washed with a saturated aqueous solution of sodium chloride (50 ml) and dried with anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+10% dichloromethane, successively) and a white glass solid (5.5 g, 60%) was obtained.

Workup

  1. temperatureunder refluxing for 10 hours
  2. waitleft
  3. waitstanding for one night
  4. customThe formed organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride (50 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, the solvent was removed by distillation
  8. customa yellow oil was obtained
  9. customThe obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+10% dichloromethane

Sources & evidence

ORD record
ord-549971c4c8dd4966a5ebc842d9bf585c
Source dataset
uspto-grants-2006_05
Patent number
US07053255B2

Reaction notes

Loading…