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Hydrochloric Acid → 2'-Chloro-2-chloro-5-methoxy-[1,1'-biphenyl]-4-carboxylic acid

HRID 1830060
Notes
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Reaction equation

HRID 1830060 reaction equation
I[C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:11][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([O:12][CH3:13])=[CH:3][C:2]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 167918585-Chloro-4-iodo-2-methoxybenzoic acid

Product 1

HCID 219477112'-Chloro-2-chloro-5-methoxy-[1,1'-biphenyl]-4-carboxylic acidYield 74.8%

Reagents, catalysts & solvents 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-iodo-5-chloro-2-methoxy benzoic acid of Example 5, Step A (3.38 g, 10.8 mmol) in N,N-dimethylformamide (80 mL) was added 2-chloro phenyl boronic acid (5.07 g, 32.4 mmol) and potassium carbonate (3.44 g, 32.4 mmol). This mixture was purged with nitrogen and then treated with tetrakis(triphenylphosphine) palladium(0) (0.625 g, 0.54 mmol). The reaction was heated to reflux overnight, cooled, acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to provide 2.4 g of the title acid which was used in the next step without further purification.

Workup

  1. customThis mixture was purged with nitrogen
  2. temperatureThe reaction was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-2b0fd1a23224442481cd138c871a7f2f
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07064120B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes