Ethyl bromoacetate → Ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate

HRID 1771590Notes

Reaction equation

HRID 1771590 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.CC([O-])(C)C.[K+].Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[O:23][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 894450523-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

Product 1

HCID 89443544Ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetateYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol (300 mg, 0.96 mmol, 1.0 eq.) and t-BuOK (216 mg, 1.90 mmol, 2.0 eq) in DMF (3 mL) was added dropwise ethyl bromoacetate (193 mg, 128 uL, 1.20 mmol, 1.2 eq) at 0° C. The resulting mixture was stirred for 1 h at room temperature. The reaction was quenched with water and neutralized with 1 M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by chromatography (petroleum ether: EtOAc, 4:1) to give the title compound as a colourless oil (200 mg, 52%).

Workup

  1. customThe reaction was quenched with water and neutralized with 1 M HCl
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by chromatography (petroleum ether: EtOAc, 4:1)

Sources & evidence

ORD record
ord-638f10ed6c374e98ad9ab113cf6b7670
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…