Pyridine → (RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid ethyl ester

HRID 1247370Notes

Reaction equation

HRID 1247370 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12]([O:16][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:11][C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 69290842(RS)-(2,6-difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 69291038(RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid ethyl esterYield 65%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(RS)-(2,6-Difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester (500 mg) was dissolved in CH2Cl2 (20 ml). Cu(OAc)2 (349 mg), 4-methoxyphenylboronic acid (876 mg) and MS4 Å were added followed by pyridine (760 mg). The mixture was stirred over night before filtration and evaporation of the solvent. CC (Hept/CH2Cl2 1:4) afforded 455 mg (65%) of (RS)-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid ethyl ester. Yellow oil.

Sources & evidence

ORD record
ord-0c5bb8b23ae846c6bcb4eeb5083aa399
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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