2-Propanethiol → HCID 56945880, compound

HRID 541569Notes

Reaction equation

HRID 541569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][CH:19]([SH:21])[CH3:20]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:21][CH:19]([CH3:20])[CH3:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 56945880HCID 56945880, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-1-fluoro-2-nitrobenzene (1.0 g, 4.5 mmol) [Aldrich] and potassium carbonate (1.6 g, 11 mmol) were stirred in N,N-dimethylformamide (10 mL), and 2-propanethiol (0.42 mL, 4.5 mmol) was added. The mixture was heated to 100° C. for 16 hours. The mixture was cooled to rt, diluted with water (100 mL), and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, and evaporated to give the desired compound (1.2 g, 96%). 1H NMR (300 MHz, CDCl3): δ 8.27 (s, 1H), 7.62 (d, 1H), 7.38 (d, 1H), 3.55 (m, 1H), 1.40 (d, 6H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4f0c3899bd84488e92ef2913d9370889
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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