4-Bromotoluene → 2-Methoxy-4'-methyl-1,1'-biphenyl

HRID 458511Notes

Reaction equation

HRID 458511 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.[Br-].C([NH3+])CCC.C([O-])([O-])=O.[Na+].[Na+]>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)C.O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 78054-BromotolueneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 21904131N-butyl-ammonium bromide

Product 1

HCID 103135412-Methoxy-4'-methyl-1,1'-biphenylYield 81%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-bromotoluene, 171 mg (1 mmol), 2-methoxyphenylboronic acid, 152 mg (1 mmol), palladium diacetate, 1 mg (4 μmol), N-butylammonium bromide, 322 mg (1 mmol), and 2 M aqueous Na2CO3, 1.9 mL (3.8 mmol), were placed in a microwaveable pressure vial and heated to 150 C for 5 minutes. After cooling to room temperature, the product was poured into a separatory funnel and 30 mL each of water and diethyl ether were added. After extraction, the layers were separated and the aqueous layer washed with another 30 mL diethyl ether. The ether extracts were combined, dried over MgSO4, and the solvent removed by rotary evaporation under vacuum. 2-methoxy-4′-methylbiphenyl, 160 mg (81% yield) was obtained as a solid product, 95% purity by NMR.

Workup

  1. temperatureheated to 150 C for 5 minutes
  2. additionthe product was poured into a separatory funnel
  3. extractionAfter extraction
  4. customthe layers were separated
  5. washthe aqueous layer washed with another 30 mL diethyl ether
  6. dry with materialdried over MgSO4
  7. customthe solvent removed by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-7ad3240de48641a18c4ad5eeb19cd432
Source dataset
uspto-grants-2007_03
Patent number
US07192918B2

Reaction notes

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