Sodium Carbonate → (4-(2-Chloroethoxy)phenyl)(3-fluoro-4-hydroxyphenyl)methanone

HRID 626145Notes

Reaction equation

HRID 626145 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([F:21])[CH:14]=2)=[O:12])=[CH:7][CH:6]=1.C([O-])([O-])=O.[Na+].[Na+]>Br>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:21])[CH:14]=2)=[O:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 89656203(4-(2-Chloroethoxy)phenyl)(3-fluoro-4-methoxyphenyl)methanone

Product 1

HCID 89656051(4-(2-Chloroethoxy)phenyl)(3-fluoro-4-hydroxyphenyl)methanoneYield 51%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

(4-(2-Chloroethoxy)phenyl)(3-fluoro-4-methoxyphenyl)methanone from the previous step in 20 mL 40% HBr was refluxed for 1 h., neutralized with solid Na2CO3 at 0° C., and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography (eluent: petroleum ether/EtOAc=5/1 to 2/1) over silica gel to give the subtitle compound (731 mg, 51% yield for 3 steps) as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by column chromatography (eluent: petroleum ether/EtOAc=5/1 to 2/1) over silica gel

Sources & evidence

ORD record
ord-199cf749595d45de957133c948a279da
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…