Potassium Carbonate → (4''-Chloro-4-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-acetic acid methyl ester

HRID 426307Notes

Reaction equation

HRID 426307 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH:9]=[C:10](OS(C(F)(F)F)(=O)=O)[CH:11]=1)C.[Cl:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:1][O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[C:10]([C:35]2[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=2)[CH:9]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:22][CH:21]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 57666648(5-Trifluoromethanesulfonyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66702480(4''-Chloro-4-trifluoromethyl-[1,1';3',1'']terphenyl-5'-yl)-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (100 mg, 0.2 mmol), 4-chlorophenyl boronic acid (41 mg, 0.24 mmol), K2CO3 (2 M solution in H2O, 220 μL, 0.4 mmol) in DME (2.0 mL) was heated to 80° C. in the presence of bis(tri-t-Butylphosphine) palladium (0) (cat) for 2 hrs. The mixture was cooled to room temperature filtered, diluted with EtOAc, washed with Na2CO3, dil HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give an off white solid. The residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

Workup

  1. filtrationfiltered
  2. additiondiluted with EtOAc
  3. washwashed with Na2CO3, dil HCl, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give an off white solid
  7. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

Sources & evidence

ORD record
ord-a60f05894bb24b6dbb06173cde999b9b
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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