Sodium Carbonate → Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetate

HRID 1771600Notes

Reaction equation

HRID 1771600 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[Na+].[Na+].Br[CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([F:10])=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:18][C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 121593Isopropyl bromoacetateHCID 227559833-Amino-2,4-difluorophenol

Product 1

HCID 89444213Isopropyl 2-(3-amino-2,4-difluoro-phenoxy)acetateYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-amino-2,4-difluoro-phenol (intermediate X(a)) (713 mg, 4.91 mmol, 1.0 eq) in DMF (20 mL) was added Na2CO3 (1.56 g, 14.8 mmol, 3.0 eq). The resulting mixture was stirred at room temperature for 35 min, then isopropyl bromoacetate (1.07 g, 5.90 mmol, 1.2 eq) was added and the reaction stirred at room temperature overnight. The reaction was diluted with water then extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6) to give the title compound (intermediate IV(b)) as an oil (850 mg, 71%).

Workup

  1. stirringthe reaction stirred at room temperature overnight
  2. extractionthen 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 was purified by chromatography (EtOAc:petroleum ether, 0:1 to 1:6)

Sources & evidence

ORD record
ord-21d85328e4794c0fb05cd977bbea6f2f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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