Hydrochloric Acid → 3'-Borono-4-chlorobiphenyl-3-carboxylic acid

HRID 404960Notes

Reaction equation

B([C:4]1[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])(O)O.I[C:15]1[CH:16]=[C:17]([B:21]([OH:23])[OH:22])[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].Cl>C1(C)C=CC=CC=1.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[B:21]([C:17]1[CH:16]=[C:15]([C:4]2[CH:5]=[CH:6][C:7]([Cl:13])=[C:8]([C:9]([OH:11])=[O:10])[CH:12]=2)[CH:20]=[CH:19][CH:18]=1)([OH:23])[OH:22]

Participants

Conditions

Temperature: 75 °C

Procedure

5-Borono-2-chlorobenzoic acid (200 mg, 1 mmol), 3-iodophenylboronic acid (125 mg, 0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and PdCl2(PPh3)2 (37 mg, 0.05 mmol) were dissolved in a mixture of toluene-MeOH (17 mL:1.7 mL) and heated at 75° C. for 3 hours. The mixture was filtered through celite washed with water and the solvent was evaporated in vacuo. The formed crude residue was acidified with 2 M HCl and extracted into EtOAc and dried over anhyd. Na2SO4, evaporated solvent in vacuo to obtain crude 3′-borono-4-chlorobiphenyl-3-carboxylic acid as a reddish brown solid. The crude product was used for the next step without further purification.

Workup

filtrationThe mixture was filtered through celite
washwashed with water
customthe solvent was evaporated in vacuo
customThe formed crude residue
extractionextracted into EtOAc
customdried over anhyd
customNa2SO4, evaporated solvent in vacuo

Sources & evidence

ORD record: ord-918fe80fdb5443108331e3c160e6302e
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748632B2

Reaction notes

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