Methyl iodide → 1-bromo-4-methoxy-2-(methylsulfanyl)benzene

HRID 1199458Notes

Reaction equation

HRID 1199458 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].[C:11](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10][CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 145368032-Bromo-5-methoxybenzene-1-thiol

Product 1

HCID 109224181-bromo-4-methoxy-2-(methylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of step (c) above (140 mg) was dissolved in dry dimethyl formamide (2 ml). Potassium carbonate (114 mg) was added followed by methyl iodide (47 ml). The mixture was stirred for 2 hours, poured onto water and extracted with ethyl acetate. The ethyl acetate was washed with water and brine then dried and evaporated to leave the subtitle compound as a pale brown oil MS MW 232/4 bp 232.

Workup

  1. additionpoured onto water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate was washed with water and brine
  4. customthen dried
  5. customevaporated

Sources & evidence

ORD record
ord-2349a0b97f64496c98a8d2eb053ec862
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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