Ethyl difluoroacetate → HCID 86638499, compound

HRID 216344Notes

Reaction equation

HRID 216344 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.[F:14][CH:15]([F:21])[C:16](OCC)=[O:17]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:16](=[O:17])[CH:15]([F:21])[F:14])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 9961Ethyl difluoroacetateHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 86638499HCID 86638499, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,5-dibromopyridine (15.21 g, 64 mmol) in anhydrous toluene (150 mL) at −78° C. under nitrogen was added dropwise with n-BuLi (2.5 M in hexane, 25 mL, 62 mmol). Stirring was continued at −78° C. for 2 h, then ethyl difluoroacetate (11 g, 80 mmol) was added dropwise at −78° C. The mixture was stirred overnight while the temperature rose to room temperature. The mixture was partitioned between EtOAc and brine, the water layer was extracted with EtOAc, the combined organic extracts were dried and concentrated, flash chromatography on silica gel afforded 8.53 g of 1-(5-bromopyridin-2-yl)-2,2-difluoroethanone as white solid.

Workup

  1. stirringThe mixture was stirred overnight while the temperature
  2. customrose to room temperature
  3. customThe mixture was partitioned between EtOAc and brine
  4. extractionthe water layer was extracted with EtOAc
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb5e77370f144043b51db303a0569305
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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