4-Chlorotoluene → 4-Methylbiphenyl

HRID 382099Notes

Reaction equation

HRID 382099 reaction equation
C(P(C(C)(C)C)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.[OH-].[OH-].[C:24]1([B+2])C=CC=CC=1.ClC1C=CC(C)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[CH:6]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 78104-ChlorotolueneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 178419127HCID 178419127, compound

Product 1

HCID 125664-Methylbiphenyl

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (4.5 mg, 0.015 mmol, 1.5 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), additive (3.0 mmol), and 4-chlorotoluene (0.12 mL, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (2 mL) was added through a rubber septum. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0M NaOH (20 mL), followed by brine (20 mL). The organic layer was submitted for GC analysis giving the results tabulated below.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. additionThe reaction mixture was then diluted with ethyl acetate (30 mL)
  6. additionpoured into a separatory funnel
  7. washThe mixture was washed with 2.0M NaOH (20 mL)
  8. customgiving the results

Sources & evidence

ORD record
ord-1584ec2c995c4f77b99c6007e4fa5cad
Source dataset
uspto-grants-2001_10
Patent number
US06307087B1

Reaction notes

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