Sodium Carbonate → 2-Bromo-1,1':2',1''-terphenyl

HRID 901737Notes

Reaction equation

HRID 901737 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:15]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Br:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 830602,2'-Dibromobiphenyl

Product 1

HCID 2976732-Bromo-1,1':2',1''-terphenylYield 70.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an atmosphere of argon, 2,2′-dibromobiphenyl (9.5 g, 30 mmole), phenylboronic acid (3.7 g, 30 mmole) and tetrakis(triphenyl-phosphine)palladium(0) (1.0 g, 0.87 mmole, 3% Pd) were dissolved into toluene (75 ml). To the obtained solution, an aqueous solution of sodium carbonate (9.7 g, 92 mmole, 3 eq/46 ml) 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 over anhydrous magnesium sulfate. Then, the solvent was removed by distillation and a dark yellow oil was obtained. The obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane, successively) and a colorless oil (6.5 g, 70%) 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 over anhydrous magnesium sulfate
  7. customThen, the solvent was removed by distillation
  8. customa dark yellow oil was obtained
  9. customThe obtained oil was purified by the column chromatography (silica gel/hexane, hexane+3% dichloromethane and hexane+5% dichloromethane

Sources & evidence

ORD record
ord-32de543075d945e9a9f652d0b7b74a23
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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