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

HRID 404960
Notes
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Reaction equation

HRID 404960 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343623-Iodophenylboronic acidHCID 230053332-Chloro-5-(dihydroxyboranyl)benzoic acid

Product 1

HCID 667994763'-Borono-4-chlorobiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 21867641Toluene methanolSolvent

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

  1. filtrationThe mixture was filtered through celite
  2. washwashed with water
  3. customthe solvent was evaporated in vacuo
  4. customThe formed crude residue
  5. extractionextracted into EtOAc
  6. customdried over anhyd
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes