Ammonium Chloride → {4-[3,3-Bis-(3'-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic Acid

HRID 9342

Reaction equation

HRID 9342 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:9][CH2:10][S:11][C:12]2[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=2)=[CH:4][CH:3]=1.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.[F-:44].[K+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1COCC1>[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35]([C:27]2[CH:26]=[CH:25][C:24]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:37]4[CH:36]=[CH:35][CH:34]=[C:33]([C:32]([F:42])([F:31])[F:44])[CH:38]=4)=[CH:3][CH:4]=3)=[CH:9][CH2:10][S:11][C:12]3[CH:22]=[CH:21][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([CH3:23])[CH:13]=3)=[CH:29][CH:28]=2)[CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 10370262{4-[3,3-Bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid

Product 1

HCID 21986783{4-[3,3-Bis-(3'-trifluoromethyl-biphenyl-4-yl)-allylsulfanyl]-2-methyl-phenoxy}-acetic Acid

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (231 mg, 0.42 mmol, example 1, step A–B), 3-(trifluoromethyl)phenylboronic acid (203 mg, 1.1 mmol), KF (81 mg, 1.39 mmol), Pd2(dba)3 (23 mg, 25 mmol) and Pd(P(t-Bu)3)2 (26 mg, 51 mmol). THF (5 ml) was added to the solid mixture keeping the mixture under nitrogen. The reaction mixture was stirred at room temperature for 1 h, followed by 10 h at 50° C. A saturated solution of ammonium chloride (5 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The organic phases were dried and evaporated. The residue was purified by HPLC to give the title compound in 140 mg (49%) yield.

Workup

  1. customIn an evaporated schlenk flask kept under nitrogen atmosphere
  2. waitfollowed by 10 h at 50° C
  3. extractionthe mixture was extracted with dichloromethane (2×20 ml)
  4. customThe organic phases were dried
  5. customevaporated
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-bb4c73dfe7584f60933d4cf801180706
Source dataset
uspto-grants-2006_08
Patent number
US07091245B2

Linked notes

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