Water → HCID 68563798, compound

HRID 20426Notes

Reaction equation

HRID 20426 reaction equation
[CH2:1]([S-:4])[CH2:2][CH3:3].[Na+].[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9](F)[CH:8]=1.O>CN(C=O)C>[Br:6][C:7]1[CH:8]=[C:9]([S:4][CH2:1][CH2:2][CH3:3])[CH:10]=[C:11]([F:13])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1363131-Bromo-3,5-difluorobenzeneHCID 46817251-Propanethiol, sodium salt (1:1)

Product 1

HCID 68563798HCID 68563798, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-30 °C

Procedure

Dissolve sodium propanethiolate (7.5 g) in DMF (250 mL) at ambient temperature, then chill to −30° C. and add 1-bromo-3,5-difluorobenzene (8.35 mL). After 1 hour, warm to −15° C., and stir for an additional 3 hours. Pour into water (2 L) and extract into hexanes (3×500 mL). Wash the resulting organic solution with saturated aqueous sodium chloride (100 mL), dry (magnesium sulfate), filter and concentrate. Filter through a plug of silica gel, wash with 10:90 ethyl acetate:hexanes and concentrate to give 1-bromo-3-fluoro-5-propylsulfanylbenzene (16.2 g, 90%). The title compound is prepared essentially as described in Preparation 343.

Workup

  1. temperaturewarm to −15° C.
  2. extractionextract into hexanes (3×500 mL)
  3. washWash the resulting organic solution with saturated aqueous sodium chloride (100 mL)
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. filtrationFilter through a plug of silica gel
  8. washwash with 10:90 ethyl acetate
  9. concentrationhexanes and concentrate

Sources & evidence

ORD record
ord-329f51804cfc40caaa7624592fb201f1
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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