Cesium carbonate → HCID 53997198, compound

HRID 2258529Notes

Reaction equation

HRID 2258529 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:11][C:12]([F:26])([F:25])[C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[CH2:16]Br>CN(C)C=O>[C:1]([O:4][CH2:16][C:15]1[CH:18]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:20]=[C:13]([C:12]([F:11])([F:25])[F:26])[CH:14]=1)(=[S:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 178418634HCID 178418634, compound

Product 1

HCID 53997198HCID 53997198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thioacetic acid (5.13 ml) was added to a suspension of caesium carbonate (11.7 g) in dimethylformamide (120 ml) at room temperature. The solution was stirred for 10 min and a solution of 3,5-bis(trifluoromethyl)benzyl bromide (20 g) in dimethylformamide (10 ml) was added. The resulting solution was stirred for 16 h, in the dark. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (Na2SO4) and the solvent was removed leaving an orange oil. The off was chromatographed on silica gel in 5% ethyl acetate/petrol giving 3,5-bis(trifluoromethyl)benzyl thioacetate (14.8 g) as a yellow oil. 1H NMR (360 MHz, CDCl3) δ 2.39 (3H, s), 4.17 (2H, s), 7.75 (3H, s); m/z (CI+) 303 (M+ +1).

Workup

  1. stirringThe resulting solution was stirred for 16 h, in the dark
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed
  7. customleaving an orange oil
  8. customThe off was chromatographed on silica gel in 5% ethyl acetate/petrol

Sources & evidence

ORD record
ord-6e3f6223c9284ec29023950fee353651
Source dataset
uspto-grants-1997_08
Patent number
US05661162

Reaction notes

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