Sodium Carbonate → 2-bromo-2'-methoxy-1,1'-Biphenyl

HRID 1937800Notes

Reaction equation

HRID 1937800 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(O)C.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>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH3:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 120407242-bromo-2'-methoxy-1,1'-BiphenylYield 63%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Bromoiodobenzene (640 μL, 5.0 mmol) was added to a suspension of Pd(PPh3)4 (305 mg, 0.26 mmol) in DME (100 mL) at room temperature under argon. After 15 min at room temperature, a solution of 2-methoxyphenylboronic acid (760 mg, 5.0 mmol) in ethanol (2 mL) was added, followed by aqueous Na2CO3 (2.0 M, 5 mL, 10 mmol). The reaction vessel was fitted with a reflux condenser and heated to reflux under argon for 22.5 h. The reaction mixture was then cooled to room temperature and filtered through Celite. The filter cake was washed with ether and water, and the filtrate was concentrated in vacuo. The resulting aqueous residue was diluted with brine and extracted with ether. The ethereal layer was dried (MgSO4), filtered and concentrated. The crude residue was purified by flash chromatography on silica gel to afford 823 mg (63%) of a colorless oil.

Workup

  1. customThe reaction vessel was fitted with a reflux condenser
  2. temperatureheated
  3. temperatureto reflux under argon for 22.5 h
  4. filtrationfiltered through Celite
  5. washThe filter cake was washed with ether and water
  6. concentrationthe filtrate was concentrated in vacuo
  7. additionThe resulting aqueous residue was diluted with brine
  8. extractionextracted with ether
  9. dry with materialThe ethereal layer was dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e545dc8915364825a4d9e765ba68bd39
Source dataset
uspto-grants-2002_05
Patent number
US06395916B1

Reaction notes

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