Ethyl Acetate → Quinoxaline, 2-[(4-bromo-4,4-difluorobutyl)thio]-

HRID 725012Notes

Reaction equation

HRID 725012 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]1=[S:11].CS(O[CH2:17][CH2:18][CH2:19][C:20]([Br:23])([F:22])[F:21])(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(C)=O.CCCCCC>[Br:23][C:20]([F:22])([F:21])[CH2:19][CH2:18][CH2:17][S:11][C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27636052-QuinoxalinethiolHCID 218503894-Bromo-4,4-difluorobutyl methanesulfonate

Product 1

HCID 21850450Quinoxaline, 2-[(4-bromo-4,4-difluorobutyl)thio]-Yield 66.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

A mixture of the product from Step 1 (1 g), 4-bromo-4,4-difluorobutyl methanesulfonate (1.65 g) and potassium carbonate (0.852 g) were stirred together in acetone (30 cm3) at ambient temperature for 7 hours. Inorganic solids were removed by filtration and the filtrate evaporated under reduced pressure to give a brown oil. Chromatography on silica gel using 1:4 ethyl acetate:hexane as eluant gave 2-(4-bromo-4,4-difluorobutylthio)-quinoxaline (1.375 g). M+ =332; 1H NMR: δ 2.19(2H,m); 2.50-2.70(2H,m); 3.43(2H,t); 7.60-7.73(2H,m); 7.93(1H,dd); 8.03(1H,dd); 8.60(1H,s); (oil).

Workup

  1. customInorganic solids were removed by filtration
  2. customthe filtrate evaporated under reduced pressure
  3. customto give a brown oil

Sources & evidence

ORD record
ord-4270414e744942d09f5f3353efc56ca1
Source dataset
uspto-grants-1998_01
Patent number
US05705516

Reaction notes

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