Sodium Carbonate → 2'-Methoxymethyl-biphenyl-4-carboxylic acid

HRID 2244252Notes

Reaction equation

HRID 2244252 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120854-Iodobenzoic acidHCID 37594082-(Methoxymethyl)benzeneboronic acid

Product 1

HCID 672555592'-Methoxymethyl-biphenyl-4-carboxylic acidYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-iodobenzoic acid (0.82 g, 3.31 mmol) and 2-methoxymethylphenylboronic acid (0.55 g, 3.31 mmol) in dry acetonitrile (30 mL) was added a 0.4 M aqueous sodium carbonate solution (30 mL) and the reaction mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (90 mg, 0.078 mmol) was then added and the reaction mixture heated to 90° C. for 19 hours. The hot reaction mixture was filtered through celite, concentrated in vacuo to remove acetonitrile and the resulting aqueous suspension washed with ethyl acetate (2×30 mL). The aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid, the resulting white suspension cooled to 4° C. for 1 hour and the solid product filtered. Recrystallization from dichloroethane gave the title compound (0.469 g, 59%) as a white solid, m.p. 164.5-165.5° C.

Workup

  1. customthe reaction mixture purged with nitrogen for 10 minutes
  2. filtrationThe hot reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customto remove acetonitrile
  5. washthe resulting aqueous suspension washed with ethyl acetate (2×30 mL)
  6. additionThe aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid
  7. temperaturethe resulting white suspension cooled to 4° C. for 1 hour
  8. filtrationthe solid product filtered
  9. customRecrystallization from dichloroethane

Sources & evidence

ORD record
ord-e08fd83949e446f1a834148187aa4a06
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

Loading…