2-(Methoxymethyl)benzeneboronic acid → HCID 11515794, compound

HRID 2113012Notes

Reaction equation

HRID 2113012 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[CH:5]=1.[CH3:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>O1CCOCC1>[CH3:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:2])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 37594082-(Methoxymethyl)benzeneboronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate2×

Product 1

HCID 11515794HCID 11515794, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of intermediate 1; 37 mg, 0.1 mmol) in dioxane (2 mL) was degassed with nitrogen and then added to a reaction vial containing 2-methoxymethylphenylboronic acid (available from Apollo Scientific Ltd., Stockport, UK). The solution was sonicated and degassed and a solution of sodium hydroxide (4 M, 0.2 mL) was added, followed by bis(tri-cyclo-hexylphosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 0.005 mmol) was added. The mixture was degassed and then heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was filtered through silica and the silica washed with dioxane (1 mL), and dimethylacetamide (1 mL). 1 M HCl was added until a solid formed. The vial was centrifuged and the solvent was removed. The crude product was washed with water and centrifuged again for 5 min. The water was decanted and the solid was dried in a vacuum oven at 50 degrees to give 3-(2′-methoxymethyl-biphenyl-4-yloxymethyl)-benzoic acid. Mass spectrum MH+=349.

Workup

  1. additionadded to a reaction
  2. customThe solution was sonicated
  3. customdegassed
  4. additiona solution of sodium hydroxide (4 M, 0.2 mL) was added
  5. additionwas added
  6. customThe mixture was degassed
  7. temperatureheated in a microwave oven at 170 degrees for 25 min
  8. filtrationThe reaction mixture was filtered through silica
  9. washthe silica washed with dioxane (1 mL), and dimethylacetamide (1 mL)
  10. addition1 M HCl was added until a solid
  11. customformed
  12. customthe solvent was removed
  13. washThe crude product was washed with water
  14. customThe water was decanted
  15. customthe solid was dried in a vacuum oven at 50 degrees

Sources & evidence

ORD record
ord-c9601f4c2c5e44f3931ebeb5324b824b
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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