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Potassium Fluoride → Methyl 2'-methyl-2-(methylsulfonyl)biphenyl-4-carboxylate

HRID 219830
Notes
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Reaction equation

HRID 219830 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO.C1(C)C=CC=CC=1>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[S:12]([CH3:15])(=[O:14])=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acidHCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 67528382Methyl 2'-methyl-2-(methylsulfonyl)biphenyl-4-carboxylateYield 88.7%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a schlenk flushed with Argon were added methyl 4-chloro-3-(methylsulfonyl)benzoate (124.34 mg; 0.50 mmol; 1 eq.), o-tolylboronic acid (84.97 mg; 0.62 mmol; 1.25 eq.), palladium(II) acetate (22.45 mg; 0.10 mmol; 0.20 eq.), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (82.11 mg; 0.20 mmol; 0.40 eq.), potassium fluoride (87.14 mg; 1.50 mmol; 3 eq.), toluene (2.49 mL), MeOH (2.49 mL) and water (5.40 μl). The reaction was degassed with Ar and heated under reflux for 2 hours. Then, it was cooled down to RT. The solvents were evaporated and the crude mixture was dissolved in EtOAc, washed with water and brine and dried over MgSO4. The resulting crude product was purified by flash chromatography (c-hex/EtOAc 9:1 to 5:5), affording the title compound as a light yellow oil (135 mg; 88%). 1H NMR (DMSO-d6, 300 MHz) δ 8.89 (d, J=1.77 Hz, 1H), 8.32 (dd, J=1.77, 7.90 Hz, 1H), 7.43-7.19 (m, 5H), 4 (s, 3H), 2.76 (s, 3H), 2.09 (s, 3H). LC/MS (Method B): 305.1 (M+H)+. HPLC (max plot) 99.2%; Rt 4.51 min.

Workup

  1. customIn a schlenk flushed with Argon
  2. customThe reaction was degassed with Ar
  3. temperatureheated
  4. temperatureunder reflux for 2 hours
  5. customThe solvents were evaporated
  6. dissolutionthe crude mixture was dissolved in EtOAc
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. customThe resulting crude product was purified by flash chromatography (c-hex/EtOAc 9:1 to 5:5)

Sources & evidence

ORD record
ord-1f2d047105c649f6b7e09107e97eb42e
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes