Dichloromethane → 1-Bromo-3-chloro-4-(methylthio)benzene

HRID 732759Notes

Reaction equation

HRID 732759 reaction equation
[CH3:1][S:2][C:3]1C=[CH:7][CH:6]=[CH:5][C:4]=1CCl.[Br:11]Br.Cl[CH2:14][Cl:15].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].C(OCC)(=O)C.O>[Br:11][C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[C:14]([Cl:15])[CH:7]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 124145821-(Chloromethyl)-2-(methylsulfanyl)benzene

Product 1

HCID 573461311-Bromo-3-chloro-4-(methylthio)benzeneYield 87%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-methylsulfanyl-2-chloromethyl-benzene (3.7 g, 23 mmol), iron (130 mg, 2.3 mmol), bromine (1.2 mL, 238 mmol), and dichloromethane (150 mL). 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 4.8 g of 4-bromo-2-chloro-1-methylsulfanyl-benzene (87%).

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-07a768f86f474fc091c5edc8eaba2dde
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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