Ammonium Chloride → 1-Bromo-3-fluoro-5-(methylsulfanyl)benzene

HRID 657512Notes

Reaction equation

HRID 657512 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([F:9])[CH:3]=1.[CH3:10][S-:11].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([S:11][CH3:10])[CH:5]=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 534144401-Bromo-3-fluoro-5-(methylsulfanyl)benzeneYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50.0 g of 1-bromo-3,5-difluorobenzene and 18.2 g sodium methanethiolate were stirred at 150° C. for 15 min in 300 ml of anhydrous DMF. Subsequently, the mixture was cooled to room temperature, poured onto 1 l of saturated aqueous ammonium chloride solution and extracted three times with 200 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 48.5 g of the title compound were obtained as a pale yellow oil.

Workup

  1. extractionextracted three times with 200 ml each of EA
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0fed665e646b48949a77f488e0853f68
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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