Potassium Carbonate → 3-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl ester

HRID 1665237

Reaction equation

HRID 1665237 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1B(O)O>O1CCOCC1.O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:28]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:27]=3[F:26])=[CH:14][CH:13]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27831332,4,5-Trifluorophenylboronic acidHCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoate

Product 1

HCID 671503683-(2',4',5'-Trifluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl esterYield 77.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Bis(tricyclohexylphosphine)palladium (200 mg, 0.3 mmol) was added to a stirred solution of 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (3.68 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol) and 2,4,5-trifluorophenylboronic acid (3.5 g, 20 mmol) in 100 mL dioxane and 10 mL H2O were reacted as above and purified by flash chromatography with a gradient of 0-5% ethyl acetate in hexanes to give 2.9 g (77.9%) of 3-(2′,4′,5′-trifluoro-biphenyl-4-yloxymethyl)-benzoic acid methyl ester.

Workup

  1. customwere reacted as above and
  2. custompurified by flash chromatography with a gradient of 0-5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7aaafe799b984c40b48d34c805355444
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Linked notes

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