Potassium Carbonate → HCID 11515906, compound

HRID 2113014Notes

Reaction equation

HRID 2113014 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.C(=O)([O-])[O-].[K+].[K+].[C:26]1(B(O)O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1>O1CCOCC1.O>[C:34]1([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:19])=[CH:13][CH:14]=2)[C:35]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate2×

Product 1

HCID 11515906HCID 11515906, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of intermediate 1; 74 mg, 0.2 mmol) in dioxane/water (10:1, 4.4 mL) was degassed for 20 min and then added to a reaction vial containing potassium carbonate (82 mg, 0.6 mmol) and 1-naphthaleneboronic acid (0.6 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.). The solution was degassed for a further 2 min and then bis(tri-cyclohexylphosphine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 14 mg, 0.02 mmol) was added. The mixture was degassed for 30 seconds 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), dimethylacetamide (1 mL), and 20% methanol in dichloromethane (1 mL). The filtrate was placed in a vial and 2 M potassium hydroxide solution (0.4 mL) was added. The mixture was stirred at room temperature overnight, and then 1 M HCl was added until a solid formed (approxiamtely 2 mL). The vial was centrifuged and the solvent was removed. The product was dried overnight in the oven to give 3-(4-naphthalen-1-yl-phenoxymethyl)-benzoic acid. Mass spectrum MH+=355.

Workup

  1. additionadded to a reaction
  2. customThe solution was degassed for a further 2 min
  3. customThe mixture was degassed for 30 seconds
  4. temperatureheated in a microwave oven at 170 degrees for 25 min
  5. filtrationThe reaction mixture was filtered through silica
  6. washthe silica washed with dioxane (1 mL), dimethylacetamide (1 mL), and 20% methanol in dichloromethane (1 mL)
  7. additionwas added
  8. addition1 M HCl was added until a solid
  9. customformed (approxiamtely 2 mL)
  10. customthe solvent was removed
  11. customThe product was dried overnight in the oven

Sources & evidence

ORD record
ord-20f58d062b824f46ae76461300c3cce2
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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