Potassium Carbonate → Ethyl 2,2-difluoro-2-(quinolin-6-yl)acetate

HRID 1959646Notes

Reaction equation

HRID 1959646 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:12]([O:14][C:15](=[O:20])[C:16](Br)([F:18])[F:17])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH2:12]([O:14][C:15](=[O:20])[C:16]([F:18])([F:17])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69585Ethyl bromodifluoroacetateHCID 203985536-Iodoquinoline

Product 1

HCID 28242385Ethyl 2,2-difluoro-2-(quinolin-6-yl)acetateYield 30.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of 6-iodo-quinoline (1.0 g, 4 mmol) and Cu(0) (559 mg, 8.8 mmol) in dry DMSO was added bromodifluoro-acetic acid ethyl ester (893 mg, 4.4 mmol). The reaction mixture was stirred under N2 at 55° C. for 15 h. The mixture was poured in a solution of K2CO3 and extracted with EtOAc. The organic layer was collected and dried over MgSO4. The crude was purified by silica gel column to give the title compound as a red oil (310 mg, 30%). 1H-NMR (400 MHz, CDCl3) δ ppm 1.33 (t, 3H), 4.334 (q, 2H), 7.52 (m, 1H), 7.93 (m, 1H), 8.15 (s, 1H), 8.20-8.23 (m, 2H), 9.03 (s, 1H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. customThe crude was purified by silica gel column

Sources & evidence

ORD record
ord-7daae1b4bc994046babe47a52b368d2a
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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