Hydrochloric Acid → 3-Acetyl-4-methylthiobenzoic acid methyl ester

HRID 47429Notes

Reaction equation

HRID 47429 reaction equation
[CH3:1][O:2][C:3](=[S:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6](Br)[CH:5]=1.[CH2:13]([O:15]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:14].O.Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[S:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([C:13](=[O:15])[CH3:14])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 542561003-Bromo-4-methylthiobenzoic acid methyl ester

Product 1

HCID 545143563-Acetyl-4-methylthiobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-4-methylthiobenzoic acid methyl ester (0.86 g), 1-ethoxyvinyl tributyl tin (1.39 ml) and tetrakis triphenylphosphinepalladium (IV) (0.15 g) were combined in dioxan (50 ml) and boiled for 24 h. The mixture was cooled, water (10 ml) and conc. hydrochloric acid (1 ml) added and the mixture stirred at room temperature overnight. Solvent was removed at reduced pressure, the residue dissolved in ethyl acetate and filtered through celite. The filtrate was evaporated to dryness and the residue triturated with hexane to give 3-acetyl-4-methylthiobenzoic acid methyl ester (0.45 g) as a yellow solid. m/z (API+): 225 (MH+).

Workup

  1. temperatureThe mixture was cooled
  2. customSolvent was removed at reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate
  4. filtrationfiltered through celite
  5. customThe filtrate was evaporated to dryness
  6. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-ca2f8f265a104a84a2347392096d09e1
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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