Sodium Carbonate → 1-(2-Bromophenyl)naphthalene

HRID 901739Notes

Reaction equation

HRID 901739 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[C:9]1(B(O)O)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 118329071-(2-Bromophenyl)naphthaleneYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an atmosphere of argon, 2-bromoiodobenzene (7.0 g, 25 mmole), naphthaleneboronic acid (4.0 g, 23 mmole) and tetrakis(triphenyl-phosphine)palladium(0) (0.5 g, 0.43 mmole, 1.7% Pd) were dissolved into toluene (50 ml). To the obtained solution, an aqueous solution of sodium carbonate (7.3 g, 69 mmole, 3 eq/35 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 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 white needle crystals (5.4 g, 83%) were 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-0e70fc4405864e309d2b24691e1f65c1
Source dataset
uspto-grants-2008_04
Patent number
US07361796B2

Reaction notes

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