Water → HCID 22273515, compound

HRID 2375286Notes

Reaction equation

HRID 2375286 reaction equation
Br[CH2:2][CH2:3][C:4]([F:7])([F:6])[F:5].[Br:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:5][C:4]([F:7])([F:6])[CH2:3][CH2:2][S:15][C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 27251143-Bromo-1,1,1-trifluoropropane

Product 1

HCID 22273515HCID 22273515, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

3-Bromo-1,1,1-trifluoropropane (640 μl, 6 mmol) was added to a mixture of 4-bromothiophenol (945 mg, 5 mmol) and potassium carbonate (760 mg, 5.5 mmol) in DMF (5 ml) and the reaction mixture heated at 40° C. for 1 hour. The mixture was allowed to cool to ambient temperature and poured into water (50 ml) and extracted with EtOAc (2×30 ml). The extracts were combined, washed with brine (3×30 ml), dried (Chemelut column 1010) and evaporated to give the title compound (1.36 g, 95%) as a pale yellow oil. NMR 2.56 (m, 2H), 3.13 (t, 2H), 7.31 (d, 2H), 7.51 (d, 2H); m/z 285 (M+).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with EtOAc (2×30 ml)
  3. washwashed with brine (3×30 ml)
  4. customdried (Chemelut column 1010)
  5. customevaporated

Sources & evidence

ORD record
ord-db8b0c66d489459e8668ed8ed73342fa
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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