Potassium Carbonate → HCID 67427979, compound

HRID 1660928Notes

Reaction equation

HRID 1660928 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([O:13][C:14](=[O:17])[CH2:15][OH:16])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[OH-].[Na+]>[CH2:11]([O:13][C:14]([C:15]1[O:16][C:2]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=2[C:4]=1[NH2:5])=[O:17])[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12184Ethyl GlycolateHCID 1235582,5-Difluorobenzonitrile

Product 1

HCID 67427979HCID 67427979, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2,5-difluoro-benzonitrile (10 g, 72.0 mmol) in DMF (200 mL) was added hydroxy-acetic acid ethyl ester (8.6 mL, 86.4 mmol) followed by K2CO3 (43.7 g, 316 mmol). After 24 h at 100° C., the reaction mixture was diluted with 1 N NaOH (200 mL) and extracted with CH2Cl2 (3×150 mL). The combined organic layers were washed with 1 N NaOH (100 mL), dried, and concentrated to afford the desired product (3.35 g, 21%). 1H NMR (CDCl3): 7.39 (dd, J=9.0, 4.0 Hz, 1H), 7.21-7.15 (m, 2H), 4.90 (s, 2H), 4.45 (q, J=7.1 Hz, 2H), 1.47 (t, J=7.1 Hz, 3H).

Workup

  1. extractionextracted with CH2Cl2 (3×150 mL)
  2. washThe combined organic layers were washed with 1 N NaOH (100 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0af9019c9dc5494b9e15e6f91be6831b
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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