Dichloromethane → 4-Bromothioanisole

HRID 1824574Notes

Reaction equation

HRID 1824574 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].ClCCl.[Br:16]Br>O>[Br:16][C:4]1[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7520ThioanisoleHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 660374-Bromothioanisole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A one-liter four-necked flask equipped with a stirrer, thermometer, dropping funnel and Liebig condenser was charged with 124.2 g (1.00 mole) of thioanisole, and 0.13 g (0.001 mole) of aluminum chloride and 200 g of dichloromethane, and 160 g (1.0 mole) of bromine was added dropwise with stirring at 5° C. over 4 hours. Thereafter, the reaction was further allowed to proceed for 2 hours. After completion of the reaction, 50 g of water was added, and phase separation was effected, whereby a 4-bromothioanisole-containing organic layer was obtained. The dichloromethane was distilled off from the organic layer obtained, whereby 203.1 g of crude 4-bromothioanisolve was obtained. The purity of the thus-obtained crude 4-bromothioanisole was 90.1% as determined by gas chromatography.

Workup

  1. customA one-liter four-necked flask equipped with a stirrer
  2. additionwas added dropwise
  3. waitto proceed for 2 hours
  4. additionwas added
  5. customphase separation
  6. additionwhereby a 4-bromothioanisole-containing organic layer
  7. customwas obtained
  8. distillationThe dichloromethane was distilled off from the organic layer
  9. customobtained
  10. customwhereby 203.1 g of crude 4-bromothioanisolve was obtained

Sources & evidence

ORD record
ord-918dda4404f94340b70d3078354da82c
Source dataset
uspto-grants-2006_05
Patent number
US07041853B2

Reaction notes

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