Pyridine → 2-(4-(4-Chloro-3-fluorophenoxy)-3-fluorophenyl)ethanol

HRID 920347Notes

Reaction equation

HRID 920347 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][C:3]=1[OH:11].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=1[F:22].N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:11][C:3]2[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][OH:10])=[CH:7][C:2]=2[F:1])=[CH:15][C:14]=1[F:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 451190812-Fluoro-4-(2-hydroxyethyl)phenol

Product 1

HCID 712365732-(4-(4-Chloro-3-fluorophenoxy)-3-fluorophenyl)ethanolYield 21.9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluoro-4-(2-hydroxyethyl)phenol (22.41 mmol, 3.5 g) and (4-chloro-3-fluorophenyl)boronic acid (45 mmol, 7.82 g) in dry CH2Cl2 (150 mL) were added copper (II) acetate (4.5 mmol 0.81 g), pyridine (45 mmol, 3.55 g), and 4 A molecular sieves in turn. The mixture was stirred at room temperature under N2 for 72 hours. The reaction mixture was filtered and the filtrate was concentrated to give crude product. The crude product was purified by silica gel chromatography to provide the desired product (1.4 g, 20%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give crude product
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-740991e7e26a404a925ae4e8d108efa7
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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