Bromomethyl 4-methoxyphenyl ketone → 1-(4-Methoxyphenyl)-2-[(3-methoxyphenyl)sulfanyl]ethan-1-one

HRID 1937640Notes

Reaction equation

HRID 1937640 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[K+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:15]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:15])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 14797Potassium HydroxideHCID 849893-Methoxybenzenethiol

Product 1

HCID 101081761-(4-Methoxyphenyl)-2-[(3-methoxyphenyl)sulfanyl]ethan-1-oneYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methoxythiophenol (50.0 g, 0.356 mol) was dissolved in 700 mL of ethanol. To this mixture was added (20 g, 0.36 mol) of potassium hydroxide pellets. A total of (82.5 g, 0.36 mol) of 2-bromo-4′-methoxyacetophenone was added in small portions to keep the temperature of the reaction at approximately 25° C. The reaction was allowed to proceed at ambient temperature for three hours. The reaction was terminated by evaporation of the alcohol, which resulted in obtaining a brown oil. The oil was partitioned between 2 L of water and 1.5 L of diethylether. The ether layer was separated and washed with water, dried with anhydrous magnesium sulfate, and evaporated to a solid. The solid was crystallized from a mixture of diethylether-petroleum ether (3:1) to yield 78.5 g of the title compound as a pink crystalline solid. mp 53° C.-54° C. EA calculated for C16H16O3S: C, 66.64; H, 5.59; O, 16.64; S, 11.12. Found: C, 66.55; H, 5.87; O, 16.82; S, 10.86.

Workup

  1. customthe temperature of the reaction at approximately 25° C
  2. customThe reaction was terminated by evaporation of the alcohol, which
  3. customresulted
  4. customin obtaining a brown oil
  5. customThe oil was partitioned between 2 L of water and 1.5 L of diethylether
  6. customThe ether layer was separated
  7. washwashed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customevaporated to a solid
  10. customThe solid was crystallized from a mixture of diethylether-petroleum ether (3:1)

Sources & evidence

ORD record
ord-46bf134ff9334ef98ba37073a283d042
Source dataset
uspto-grants-2002_05
Patent number
US06395769B1

Reaction notes

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