Water → HCID 89445435, compound

HRID 1771709Notes

Reaction equation

HRID 1771709 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH2:8][NH:9][C:10]2[C:11]([F:18])=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=2[F:16])[CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:19])=[C:6]([CH2:8][NH:9][C:10]2[C:11]([F:18])=[C:12]([CH:13]=[CH:14][C:15]=2[F:16])[O:17][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 89445228HCID 89445228, compound

Product 1

HCID 89445435HCID 89445435, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[(5-bromo-2-fluoro-phenyl)methylamino]-2,4-difluoro-phenol (5.26 g, 15.8 mmol, 1.0 eq) in DMF (50 mL) was added Na2CO3 (2.35 g, 22.2 mmol, 1.4 eq). The reaction was stirred at room temperature for 30 min then ethyl bromoacetate (2.91 g, 17.4 mmol, 1.1 eq) was added. The reaction mixture was stirred at room temperature for 1 h then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 40:1 to 30:1) to give the title compound as a colorless oil (5 g, 75%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether:EtOAc, 40:1 to 30:1)

Sources & evidence

ORD record
ord-5cfadc4473d44c0ca5fbd0982c3bfa64
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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