Potassium Carbonate → Dimethyl 4-(3-bromophenylsulphanylmethyl)phthalate

HRID 2307548Notes

Reaction equation

HRID 2307548 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]1[CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[C:14](=[CH:19][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:10][C:11]2[CH:12]=[C:13]([C:21]([O:23][CH3:24])=[O:22])[C:14](=[CH:19][CH:20]=2)[C:15]([O:17][CH3:18])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80597m-BromobenzenethiolHCID 232556044-Bromomethylphthalic acid dimethyl ester

Product 1

HCID 22606944Dimethyl 4-(3-bromophenylsulphanylmethyl)phthalateYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5 g (26 mmol) of 3-bromothiophenol and 9.2 g (32 mmol) of dimethyl 4-bromomethylphthalate are dissolved in 150 mL of 2-butanone. 4 g (29 mmol) of potassium carbonate are added and the mixture is brought to reflux and stirred for 2 h. The reaction medium is then filtered and concentrated under reduced pressure and the residue is purified by chromatography on a column of silica. A yellow oil (10 g) is obtained in a yield of 100%.

Workup

  1. temperatureto reflux
  2. filtrationThe reaction medium is then filtered
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is purified by chromatography on a column of silica

Sources & evidence

ORD record
ord-9f5a235766624b5fb1c49602789d8351
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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