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

HRID 1752589Notes

Reaction equation

HRID 1752589 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

Conditions

Temperature
55 °C

Procedure

A mixture of 2-bromoquinoline (5.0 g, 24.0 mmol), ethyl 2-bromo-2,2-difluoroacetate (5.8 g, 28.8 mmol) and copper power (3.5 g, 55.2 mmol) in DMSO (20 ml) was stirred at 55° C. for 5 hours. The solid was filtered off and water (100 ml) and EA (150 ml) were added. The organic layer was separated and evaporated and concentrated to give the title product (4.2 g, 70%) which was used for the next step without further purification. LC-MS (ESI+): m/e 252 (M+H)+, Rt: 0.934 min/2.5 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. customevaporated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e223211909e94354839bd2530332c1cd
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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