Hydrochloric Acid → 3-(3-Methoxycarbonylphenyl)benzoic acid

HRID 42541

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][O:12][C:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:11][O:12][C:13]([C:15]1[CH:16]=[C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=2)[CH:18]=[CH:19][CH:20]=1)=[O:14]

Participants

Conditions

Temperature: 40 °C

Procedure

3-Iodobenzoic acid (1.0 g, 4.03 mmol, 1 equiv.), 3-(methoxycarbonyl)phenylboronic acid (0.73 g, 4.03 mmol, 1 equiv.), and Pd(OAc)2 (27 mg, 0.12 mmol, 0.03 equiv.) were mixed in DMF (10 mL) at RT with stirring, followed by the addition of 1.5M cesium carbonate (8.06 mL, 1.16 mmol, 3 equiv.). The mixture was heated at 40° C. for 4 hours. At the conclusion of this period, the reaction was worked up by adding water and adjusting the pH to 3 with 1N HCl. The aqueous mixture was extracted (3×) with EtOAc/THF. The organic layers were rinsed (3×) with water. The organic layer was dried over sodium sulfate and concentrated to give an off-white solid. The solid was stirred in hexanes (10 mL), filtered and dried under high vacuum to give 3′-(methoxycarbonyl)biphenyl-3-carboxylic acid (860 mg, 3.36 mmol, 83% yield) as a white solid. MS (ESI+)=257.23 (M+H)+.

Workup

extractionThe aqueous mixture was extracted (3×) with EtOAc/THF
washThe organic layers were rinsed (3×) with water
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated
customto give an off-white solid
filtrationfiltered
customdried under high vacuum

Sources & evidence

ORD record: ord-9515ed8835e540f496bf50d91c6a761f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536198B2

Linked notes

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