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Sodium Carbonate → 3-Chloro-5'-fluoro-2'-methoxy-[1,1'-biphenyl]-4-carboxylic acid

HRID 1891421
Notes
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Reaction equation

HRID 1891421 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:22][CH3:23])=[C:17](B(O)O)[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)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:4]1[CH:3]=[C:2]([C:15]2[CH:14]=[C:13]([F:12])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 1088294-Bromo-2-chlorobenzoic acidHCID 27826735-Fluoro-2-methoxyphenylboronic acid

Product 1

HCID 251528833-Chloro-5'-fluoro-2'-methoxy-[1,1'-biphenyl]-4-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

4-Bromo-2-chlorobenzoic acid (1.1 g) and 5-fluoro-2-methoxyphenylboronic acid (0.94 g) were suspended in toluene (20 mL) and ethanol (20 mL). Aqueous 2M sodium carbonate solution (16 mL) and tetrakis(triphenylphosphine) palladium(0) (0.14 g) were added and the reaction was heated at 95° C. for 20 h. The mixture was diluted with water, extracted with diethyl ether (discarded). The aqueous layer was acidified with aqueous 2M hydrochloric acid, extracted with ethyl acetate, dried (MgSO4) and concentrated under reduced pressure to give the sub titled product as a cream solid (1.25 g).

Workup

  1. extractionextracted with diethyl ether (discarded)
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db53b110bdac418ab14badacf7bf4aa3
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507544B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes