Hydrochloric Acid → Methyl 2-(3-methoxyphenylthio)phenylacetate

HRID 129593

Reaction equation

HRID 129593 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=[O:20].Cl.[CH3:23]N(C=O)C>[Cu]Cl.CO.O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([S:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][C:19]([O:21][CH3:23])=[O:20])[CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 849893-MethoxybenzenethiolHCID 877542-Bromophenylacetic acidHCID 5360545Sodium

Product 1

HCID 14674865Methyl 2-(3-methoxyphenylthio)phenylacetateYield 91%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of the sodium salt of 3-methoxythiophenol [prepared by treatment of 3-methoxythiophenol (2.8 g) with sodium hydroxide (0.8 g) in methanol (20 ml) followed by evaporation to dryness], 2-bromophenylacetic acid (4.3 g) and copper(I) chloride (0.4 g) in dry DMF (25 ml) was heated overnight at reflux. The reaction mixture was cooled, poured into water and acidified with dilute hydrochloric acid. The aqueous mixture was extracted with ether (×3) and the combined ether extracts were extracted in turn with dilute sodium hydroxide solution (×2). The combined aqueous hydroxide extracts were acidified with dilute hydrochloric acid and re-extracted with ether (×3). These combined ether extracts were washed with water (×3), dried and evaporated to give an orange oil (3.5 g, 96.8% by GC). The oil was treated with acidic methanol overnight at room temperature. Normal work-up afforded methyl 2-(3-methoxyphenylthio)phenylacetate (2.9 g, 91% by GC) as a yellow liquid which was used in the next stage without further purification.

Workup

  1. temperaturewas heated overnight
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. extractionThe aqueous mixture was extracted with ether (×3)
  5. extractionthe combined ether extracts were extracted in turn with dilute sodium hydroxide solution (×2)
  6. extractionre-extracted with ether (×3)
  7. washThese combined ether extracts were washed with water (×3)
  8. customdried
  9. customevaporated
  10. customto give an orange oil (3.5 g, 96.8% by GC)

Sources & evidence

ORD record
ord-540b33ba3e3342d4a5ec8156a8794b81
Source dataset
uspto-grants-1995_11
Patent number
US05468857

Linked notes

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