Potassium Carbonate → HCID 11654119, compound

HRID 2113015Notes

Reaction equation

HRID 2113015 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+].[O:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCOCC1.O>[O:26]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=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)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2773559(2-Phenoxyphenyl)boronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate

Product 1

HCID 11654119HCID 11654119, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A degassed solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (of Inter-mediate 1; 74 mg, 0.2 mmol) in dioxane (4 mL) and a degassed solution of potassium carbonate (83 mg) in water (0.4 mL) were added to a reaction vial containing (2-phenoxy)phenylboronic acid (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.; 128 mg, 0.6 mmol). The solution was degassed and bis(tri-cyclohexylphos-phine)palladium (available from Strem Chemicals, Inc., Newburyport, Mass.; 7 mg, 0.01 mmol) was added. The mixture was heated in a microwave oven at 170 degrees for 25 min. The reaction mixture was filtered through silica, and washed with dioxane (1 mL) and dimethylacetamide (1 mL). 2 M potassium hydroxide solution (0.4 mL) was added. The mixture was stirred at room temperature overnight, and then 1 M HCl (0.8 mL) was added. The solvent was evaporated and the residue was triurated with 50% aqueous methanol to give 3-(2′-phenoxy-biphenyl-4-yloxymethyl)-benzoic acid. Mass spectrum MH+=397.

Workup

  1. customThe solution was degassed
  2. temperatureThe mixture was heated in a microwave oven at 170 degrees for 25 min
  3. filtrationThe reaction mixture was filtered through silica
  4. washwashed with dioxane (1 mL) and dimethylacetamide (1 mL)
  5. addition2 M potassium hydroxide solution (0.4 mL) was added
  6. addition1 M HCl (0.8 mL) was added
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a8d3e094973946e8921407033350a48b
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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