Ethyl bromodifluoroacetate → Ethyl α,α-difluoro-2-quinolineacetate

HRID 920893Notes

Reaction equation

HRID 920893 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[C:13]([F:20])([F:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CS(C)=O.[Cu]>[CH2:17]([O:16][C:14](=[O:15])[C:13]([F:20])([F:19])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH3:18]

Participants

5

Reactant 2

HCID 69585Ethyl bromodifluoroacetateHCID 27627562-Bromoquinoline

Product 1

HCID 10514875Ethyl α,α-difluoro-2-quinolineacetateYield 70%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromoquinoline (5.0 g, 24.0 mmol), ethyl 2-bromodifluoroacetate (5.8 g, 28.8 mmol) and copper powder (3.5 g, 55.2 mmol) in DMSO (20 mL) were stirred at 55° C. for 5 hours. The solid was filtered off, water (100 mL) and EA (150 mL) were added. The organic layer was separated, dried over sodium sulfate and concentrated to give the title compound as a yellow oil (4.2 g, 70%), which was used in the next step without further purification. LC-MS (ESI+): m/e 252 (M+H)+, Rt: 0.93 min.

Workup

  1. filtrationThe solid was filtered off
  2. additionwater (100 mL) and EA (150 mL) were added
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b75998b1f58a4aac89933d1299280816
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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