Bromine → 4-Bromo-1-(methylthio)-2-(trifluoromethyl)-benzene

HRID 732764Notes

Reaction equation

HRID 732764 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[Br:13]Br.[Cl-].[Al+3].[Cl-].[Cl-].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].C(OCC)(=O)C.O.ClCCl>[Br:13][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:5]=1

Participants

9

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 27607832-TrifluoromethylthioanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 223153184-Bromo-1-(methylthio)-2-(trifluoromethyl)-benzeneYield 83%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-methylsulfanyl-2-trifluoromethyl-benzene (3.5 g, 18 mmol), iron (100 mg, 1.79 mmol), bromine (0.95 mL, 18 mmol), aluminum chloride (242 mg, 1.8 mmol) and dichloromethane (50 mL) and stir for 2 hours. Add water (10 mL), aqueous saturated sodium thiosulfate (100 mL) and ethyl acetate (100 mL). Separate the organic layer and wash with brine, dry with MgSO4, filter and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with hexane to give 3.6 g of 4-bromo-1-methylsulfanyl-2-trifluoromethyl-benzene (83%).

Workup

  1. customSeparate the organic layer
  2. washwash with brine
  3. dry with materialdry with MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. washChromatograph the residue on a SiO2 column eluting with hexane

Sources & evidence

ORD record
ord-650a0fb5d0ad4d1c8dee7fa1289afb03
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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