Potassium Carbonate → 3-Bromo-2-methoxy-1,1'-biphenyl

HRID 1042509Notes

Reaction equation

HRID 1042509 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[C:12]=1[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[Br:17][C:13]1[C:12]([O:18][CH3:19])=[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 181584Benzene, 1,3-dibromo-2-methoxy-

Product 1

HCID 183474973-Bromo-2-methoxy-1,1'-biphenylYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of phenylboronic acid (3.4 g, 28.7 mmol), 2,6-dibromoanisole (22.3 g, 83.8 mmol, 3 equiv.) and palladium tetrakistriphenylphosphine (0.6 g) in ethylene glycol dimethyl ether (50 mL) and a solution of potassium carbonate (10.8 g, 0.078 mol) in water (50 mL) were kept at reflux under nitrogen with good stirring overnight. After cooling, the reaction mixture was partitioned between ethyl acetate (800 mL) and water (400 mL). The organic phase was washed with water (2×400 mL), dried over sodium sulfate and filtered. The solvent was removed in vacuo and the residue was chromatographed on silica (360 g) with heptane (5 L) to afford 6.55 g of pure product (87%).

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (800 mL) and water (400 mL)
  4. washThe organic phase was washed with water (2×400 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was chromatographed on silica (360 g) with heptane (5 L)

Sources & evidence

ORD record
ord-5a56c11120814a7aaa5d0cc913386c4c
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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