Triethylamine → (RS)-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-ethoxy-acetic acid ethyl ester

HRID 1247385Notes

Reaction equation

HRID 1247385 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2].[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([O:16][C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[C:10]=1[F:17])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 69290130(RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester

Product 1

HCID 69290936(RS)-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-ethoxy-acetic acid ethyl esterYield 35.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution under Ar of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-ethoxy-acetic acid ethyl ester (320 mg) in CH2Cl2 (10 ml) was added copper(II)acetate (230 mg), 4-fluorobenzeneboronic acid 516 mg) and powdered MS4 Å (2 g). After addition of triethlyamine (622 mg) the mixture was stirred 40 h at rt. The solids were filtered away and the solvent was evaporated. Column chromatography (CC) (AcOEt:Hept 1:9 to 1:1) afforded 154 mg of (RS)-[2,6-difluoro-3-(4-fluoro-phenoxy)-phenyl]-ethoxy-acetic acid ethyl ester as a brownish oil.

Workup

  1. filtrationThe solids were filtered away
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2abcf38dc52b4f92ae5c5e85f5db6838
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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