Water → HCID 67253353, compound

HRID 1711626Notes

Reaction equation

HRID 1711626 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[OH:20].N1C=CC=CC=1.O>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[O:20][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 935762-Methyl-5-nitrophenolHCID 27343783-Pyridinylboronic acid

Product 1

HCID 67253353HCID 67253353, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine-3-boronic acid (0.68 g, 5.5 mmol) and 2-methyl-5-nitro phenol (0.85 g, 5.5 mmol) in DCM (10 mL) was treated with pyridine (1.00 mL, 12.4 mmol), copper acetate (1.5 g, 8.3 mmol) and powdered 4A molecular sieves (330 mg). The reaction mixture was stirred for 7 days at RT open to air. The mixture was poured into water (50 mL) and extracted with DCM (2×50 mL). The combined organic phases were washed with saturated aq NaHCO3 (25 mL), water (25 mL), satd NH4Cl (2×25 mL) and brine (25 mL), dried (Na2SO4), concentrated in vacuo and purified via chromatography on silica gel to provide 3-(2-methyl-5-nitrophenoxy)pyridine (81 mg, 6% yield). 1H NMR (400 MHz, CDCl3) δ 8.48 (dd, J=4.6, 1.0 Hz, 1H), 8.43 (d, J=2.4 Hz, 1H), 7.99 (dd, J=8.0, 2.0 Hz, 1H), 7.70 (d, J=2.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.39-7.30 (m, 2H), 2.42 (s, 3H); MS (ESI) m/z: 231.0 (M+H+).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined organic phases were washed with saturated aq NaHCO3 (25 mL), water (25 mL), satd NH4Cl (2×25 mL) and brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified via chromatography on silica gel

Sources & evidence

ORD record
ord-9034e746365048d8a8223096be3cc9e5
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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