Thioanisole → 1-Propanone, 2-bromo-2-methyl-1-[4-(methylthio)phenyl]-

HRID 376978Notes

Reaction equation

HRID 376978 reaction equation
[CH3:1][CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C1(SC)C=CC=CC=1.CC(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)(C1C=CC(OCC(O)COC(C=C)=O)=CC=1)C.ClS(O)(=O)=O.[Br:62]Br>C(Cl)Cl>[Br:62][C:2]([CH3:13])([CH3:1])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 5

HCID 7520ThioanisoleHCID 24408BromineHCID 24638Chlorosulfonic acidHCID 92212Bisphenol A diglycidyl ether diacrylateHCID 8525392-Methyl-1-[4-(methylthio)phenyl]-1-propanone

Product 1

HCID 114599841-Propanone, 2-bromo-2-methyl-1-[4-(methylthio)phenyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

149.2 g (0.77 mol) of 2-methyl-1-[4-(methylthio)-phenyl]-propan-1-one, prepared by acylating thioanisol (as is described in EP-A-3002), are dissolved in 770 ml of methylene chloride. 0.2 ml of chlorosulfonic acid and 123.0 g (0.77 mol) of bromine are added dropwise slowly to this solution, with cooling, at room temperature. After stirring overnight, the solution is concentrated and is then reacted further as described below.

Workup

  1. concentrationthe solution is concentrated
  2. customis then reacted further

Sources & evidence

ORD record
ord-e77ae36f6500489489741b2cc5e65a3d
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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