Potassium Carbonate → Methyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate

HRID 538503Notes

Reaction equation

HRID 538503 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([NH2:12])=[O:11].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C.O>[NH2:12][C:10]([C:3]1[C:2]([F:1])=[C:7]([CH:6]=[CH:5][C:4]=1[F:9])[O:8][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 451201362,6-Difluoro-3-hydroxybenzamide

Product 1

HCID 59402740Methyl 2-[3-(aminocarbonyl)-2,4-difluorophenoxy]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-difluoro-3-hydroxybenzenecarboxamide (1.2 g, 7 mmol, 1 equiv.), K2CO3 (2.87 g, 21 mmol, 3 equiv.) and methyl bromoacetate (0.69 ml, 7.35 mmol, 1.05 equiv.) in DMF (30 ml) was stirred at r.t. for 18 h. The mixture was diluted with water and extracted with EtOAc (4×80 ml). The combined organic extracts were dried (MgSO4) and evaporated to dryness under reduced pressure. The product was used crude on the next step. HPLC-MS (method 1): m/z 246 [M+H]+, Rt=2.08 min.

Workup

  1. extractionextracted with EtOAc (4×80 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5673516566eb4bd1a4937ed1e84bb654
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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