Sodium Hydroxide → 5-[[4-(4-methylphenyl)phenoxy]methyl]furan-2-carboxylic Acid

HRID 1176776Notes

Reaction equation

C[O:2][C:3]([C:5]1[O:6][C:7]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)=[O:4].[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[OH-].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:15]2[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:7]3[O:6][C:5]([C:3]([OH:2])=[O:4])=[CH:9][CH:8]=3)=[CH:13][CH:14]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-(4-iodo-phenoxymethyl)-furan-2-carboxylic acid methyl ester (Intermediate 6; 100 mg, 0.28 mmol), 4-methyl-phenyl-boronic acid (42 mg, 0.31 mmol), sodium hydroxide (45 mg, 1.13 mmol), palladium(II) acetate (2 mg, 0.01 mmol) and water (10 mL) was heated at ˜50° C. overnight. The mixture was filtered and the residue was washed with water, ethyl acetate, methylene chloride, and methanol. The aqueous layer was acidified and extracted three times with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried (magnesium sulfate), filtered, and evaporated to give 5-(4′-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid (80 mg, 84%) as a white solid.

Workup

filtrationThe mixture was filtered
washthe residue was washed with water, ethyl acetate, methylene chloride, and methanol
extractionextracted three times with ethyl acetate
washThe combined organic layers were washed with water and saturated brine
dry with materialdried (magnesium sulfate)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-bca941b5f22641f7af026f67826aa41e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842825B2

Reaction notes

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