Potassium Carbonate → 2-(4-Bromo-3,4,4-trifluorobutylthio)thiazole

HRID 725003Notes

Reaction equation

HRID 725003 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Br:7][C:8]([F:15])([F:14])[CH:9]([F:13])[CH2:10][CH2:11]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:7][C:8]([F:15])([F:14])[CH:9]([F:13])[CH2:10][CH2:11][S:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27834041,4-Dibromo-1,1,2-trifluorobutaneHCID 178527881HCID 178527881, compound

Product 1

HCID 218505172-(4-Bromo-3,4,4-trifluorobutylthio)thiazoleYield 96.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Mercaptothiazole (11.7 g) in acetone (30 cm3) containing 1,4-dibromo-1,1,2-trifluorobutane (27.0 g) was treated portionwise with anhydrous potassium carbonate (13.8 g) under an atmosphere of nitrogen. The reaction was stirred for 1.5 hours, filtered and the insolubles washed with further acetone (4×25 cm3). The filtrate was evaporated under reduced pressure and the residue fractionated by chromatography (silica, eluant 10% ethyl acetate in hexane) to give 2-(4-bromo-3,4,4-trifluorobutylthio)thiazole (29.5 g). 1H NMR: δ 2.2-2.5(2H,m); 3.2-3.6(2H,m); 4.7-5.0(1H,m); 7.23(1H,d); 7.68(1H,d).

Workup

  1. filtrationfiltered
  2. washthe insolubles washed with further acetone (4×25 cm3)
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-095f3b197e044ad49d2a696423a78f70
Source dataset
uspto-grants-1998_01
Patent number
US05705516

Reaction notes

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