Hydrochloric Acid → 6-Hydroxy[1,1′-biphenyl]-3-carboxylic acid

HRID 1171494Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

3-Bromo-4-hydroxybenzoic acid (500 mg, 2.30 mmol, 1 eq.), phenylboronic acid (281 mg, 2.30 mmol, 1 eq.), palladium(II)acetate (16 mg, 0.069 mmol, 0.03 eq.) and 1.5M cesium carbonate (aqueous) (4.61 mL) were dissolved in DMF (10 mL) at room temperature under nitrogen then heated at 45° C. for 20 hours. Worked up by adding water (10 mL) then adjusting to pH=3 with 1N HCl. Extracted the acidic aqueous 3 times with ethyl acetate. The ethyl acetate layers were combined and rinsed 3 times with water (10 mL). The ethyl acetate layer was then dried over sodium sulfate and stripped to an oil. The oil was purified over silica gel in 1:1 hexanes/ethyl acetate. Obtained 3-phenyl-4-hydroxybenzoic acid (330 mg) as an oil which eventually solidified. Yield=67%. LCMS detects (M+H)+=257.23.

Workup

extractionExtracted the acidic aqueous 3 times with ethyl acetate
washrinsed 3 times with water (10 mL)
dry with materialThe ethyl acetate layer was then dried over sodium sulfate
customThe oil was purified over silica gel in 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record: ord-b3e41d06e47c44a7ab0e47f879fd4ead
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829571B2

Reaction notes

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