Ethyl bromoacetate → Ethyl 2-[2,4-dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate

HRID 1771683Notes

Reaction equation

HRID 1771683 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[CH:12][C:11]=2[F:23])=[C:6]([Cl:24])[CH:5]=[CH:4][C:3]=1[OH:25].C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C=O)C>[Cl:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH:13]=[CH:12][C:11]=2[F:23])=[C:6]([Cl:24])[CH:5]=[CH:4][C:3]=1[O:25][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 894452242,4-Dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol

Product 1

HCID 89793178Ethyl 2-[2,4-dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol (150 mg, 0.4 mmol, 1.0 eq) in DMF (50 mL), was added K2CO3 (220 mg, 0.6 mmol, 1.5 eq) and the solution was stirred at room temperature for 30 min. BrCH2CO2Et (100 mg, 1.6 mmol, 4.0 eq) was added dropwise and the reaction was stirred overnight. The reaction was quenched by addition of water (200 mL) and extracted with EtOAc. The combined organic extracts were dried (Mg2SO4), filtered and evaporated under reduced pressure and the residue obtained purified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:10) to give the title compound (130 mg, 70%).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched by addition of water (200 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried (Mg2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customthe residue obtained
  8. custompurified by column chromatography (EtOAc:petroleum ether, 0:1 to 1:10)

Sources & evidence

ORD record
ord-fcb5703a3e1445c8870728a25fa46a74
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…