Phenylboronic Acid → 3-Chloro-4-methyl-1,1'-biphenyl

HRID 1828794Notes

Reaction equation

HRID 1828794 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH3:9].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.CCO.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

7

Reactant 2

HCID 66827Phenylboronic AcidHCID 28013292-Chloro-4-iodotoluene

Product 1

HCID 216510253-Chloro-4-methyl-1,1'-biphenylYield 99.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a suspension of tetrakis(triphenylphosphine)palladium (213 mg) in toluene (7 ml) was added 2-chloro-4-iodotoluene (2.33 g) at room temperature. The mixture was stirred at room temperature for 30 min, and thereto were added a solution of phenylboronic acid (1.35 g) in EtOH (2 ml) and 2M aqueous sodium carbonate solution (9.25 ml), and the mixture was refluxed under heating. After 3 hr, the reaction mixture was cooled and the organic layer was separated. The aqueous layer was extracted with hexane (4 ml). The organic layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution (4 ml) and saturated brine (4 ml), and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated, and hexane (10 ml) and silica gel (4 g) were added to the residue (2.11 g). The mixture was stirred at room temperature for 1 hr. Silica gel was filtered off and the filtrate was concentrated to give 2-chloro-4-phenyltoluene as a pale-brown oil (1.86 g, 99.4%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating
  3. waitAfter 3 hr
  4. temperaturethe reaction mixture was cooled
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with hexane (4 ml)
  7. washwashed with saturated aqueous sodium hydrogencarbonate solution (4 ml) and saturated brine (4 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated
  11. additionhexane (10 ml) and silica gel (4 g) were added to the residue (2.11 g)
  12. stirringThe mixture was stirred at room temperature for 1 hr
  13. filtrationSilica gel was filtered off
  14. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2c73b43d01dc4f22bb7efc6d2412146b
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

Loading…