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

HRID 1416315Notes

Reaction equation

HRID 1416315 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 22-2.5(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-8980ad2e62fd4c4493ced44f803e5710
Source dataset
uspto-grants-1999_06
Patent number
US05912243

Reaction notes

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