Dimethylformamide → HCID 91876369, compound

HRID 918785Notes

Reaction equation

HRID 918785 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1F.[CH2:13]([SH:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:15][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 1424144-Bromo-3-fluorobenzotrifluoride

Product 1

HCID 91876369HCID 91876369, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1.5 g of 4-bromo-3-fluorobenzotrifluoride, 0.46 ml of ethanethiol, 851 mg of potassium carbonate and 2 ml of DMF was stirred at 75° C. for 2.5 hours. Water was poured to the cooled reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.15 g of 4-bromo-3-ethylsulfanylbenzotrifluoride.

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13081a8ed97b41faba1cd5e397742ba7
Source dataset
uspto-grants-2016_03
Patent number
US09271500B2

Reaction notes

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