Thioanisole → 4-Bromothioanisole

HRID 1824573Notes

Reaction equation

HRID 1824573 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9]Br>[Fe](Cl)Cl.O>[Br:9][C:4]1[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 7520ThioanisoleHCID 24408Bromine

Product 1

HCID 660374-BromothioanisoleYield 99.9%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °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 0.32 g (0.002 mole) of iron(II) chloride, and 160 g (1.0 mole) of bromine was added dropwise with stirring at 50° C. over 4 hours. Thereafter, the reaction was further allowed to proceed for 1 hour. After completion of the reaction, 50 g of water was added, and the organic layer was separated, whereby 202.9 g of crude 4-bromothioanisole was obtained. The purity of the thus-obtained crude 4-bromothioanisole was 90.3% 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 1 hour
  4. additionwas added
  5. customthe organic layer was separated

Sources & evidence

ORD record
ord-433cdba8fd4b4823aab58dfa6ab4d097
Source dataset
uspto-grants-2006_05
Patent number
US07041853B2

Reaction notes

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