Potassium ethanethioate → thioacetic acid S-(4-bromo-2-trifluoromethyl-benzyl) ester

HRID 1093943Notes

Reaction equation

HRID 1093943 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C:14]([O-:17])(=[S:16])[CH3:15].[K+]>CC(C)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:16][C:14](=[O:17])[CH3:15])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 59623728thioacetic acid S-(4-bromo-2-trifluoromethyl-benzyl) esterYield 96.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-2-trifluoromethylbenzyl bromide (2.4 g) in acetone (20 ml) was added potassium thioacetate (1.04 g). The reaction mixture was heated to reflux for 4 hours. The reaction mixture was allowed to cool to ambient temperature and was then filtered through a plug of silica gel. Further acetone (30 ml) was passed through the silica gel (30 ml). The combined filtrate was concentrated to give thioacetic acid S-(4-bromo-2-trifluoromethyl-benzyl) ester as a dark liquid (2.275 g). 1H-NMR (400 MHz, CDCl3): 7.75 (s, 1H), 7.60 (d, 1H), 7.42 (d, 1H), 4.25 (s, 2H), 2.36 (s, 3H) ppm.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationwas then filtered through a plug of silica gel
  4. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-4568b945665f45c1a055e1558350cc9d
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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