4-Bromoanisole → 4-Methoxy-4'-methylbiphenyl

HRID 2121067Notes

Reaction equation

HRID 2121067 reaction equation
B(O)(O)[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1>O>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 10340Sodium CarbonateHCID 79799Tolylboronic acid

Product 1

HCID 17047594-Methoxy-4'-methylbiphenylYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel were placed p-tolylboronic acid (0.177 g, 1.3 mmol) and (GLCAphos)2PdCl2 (11 mg, 0.01 mmol), and the atmosphere was replaced with argon. To the mixture were added water (2 ml), an aqueous solution of sodium carbonate (2M solution, 1 ml, 2 mmol) and 4-methoxybromobenzene (0.125 ml, 1.0 mmol) as an aryl halide derivative at room temperature and the mixture was heated at 80° C. with stirring for 16 hours. During the reaction, a white solid was gradually precipitated. After cooling to room temperature, toluene (10 ml) was added to extract the product. The organic layer was washed with water five times and dried under a reduced pressure to give a substantially pure 4-methoxy-4′-methylbiphenyl in an yield of 95%.

Workup

  1. customIn a reaction vessel were placed
  2. customDuring the reaction
  3. customa white solid was gradually precipitated
  4. additiontoluene (10 ml) was added
  5. extractionto extract the product
  6. washThe organic layer was washed with water five times
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-7c37c18307894bbb89357cd8d69af448
Source dataset
uspto-grants-2004_02
Patent number
US06693210B2

Reaction notes

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