1,2-Dimethoxyethane → 3-Chloro-4-methyl-1,1'-biphenyl

HRID 1422338Notes

Reaction equation

HRID 1422338 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[CH3:9].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Ba+2].[OH-].COCCOC>O>[Cl:1][C:2]1[CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH3:9]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 28013292-Chloro-4-iodotolueneHCID 6093286Barium hydroxide

Product 1

HCID 216510253-Chloro-4-methyl-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-4-iodotoluene(2.94 g, 11.63 mmol), phenyl boronic acid (1.56 g, 12.79 mmol), barium hydroxide (5.50 g, 17.44 mmol), DME (3 mL) and water (15 mL) was purged with dry argon. Tetrakis(triphenyl-phosphine)palladium(O) (672 mg, 0.58 mmol) was added, and the resultant solution was stirred at 80° C. for 4 hours. The solvents were evaporated in vacuo, and the residue partitioned between EtOAc and water and acidified with 1M aq. HCl. The aqueous extract was separated, and extracted with EtOAc. The organic extracts were combined, washed with NaHCO3 and 5% aq. Na2S2O3, dried, (Na2SO4) filtered and the solvent evaporated in vacuo. The residue was purified by chromatography (Silica gel, 10% EtOAc in hexanes) to afford the title compound. 1H NMR (CDCl3 400 MHz) δ 7.62-7.54 (3H, m), 7.48-7.25(5H, m) and 2.43(3H, s) ppm.

Workup

  1. customwas purged with dry argon
  2. customThe solvents were evaporated in vacuo
  3. customthe residue partitioned between EtOAc and water
  4. extractionThe aqueous extract
  5. customwas separated
  6. extractionextracted with EtOAc
  7. washwashed with NaHCO3 and 5% aq. Na2S2O3
  8. customdried
  9. filtration(Na2SO4) filtered
  10. customthe solvent evaporated in vacuo
  11. customThe residue was purified by chromatography (Silica gel, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d8177d4865fd409eaddd70472f7c0f6c
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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