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

HRID 618192Notes

Reaction equation

HRID 618192 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-9576c5bc613a4ad8914a81d5554ab451
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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