Ethyl bromoacetate → Ethyl 2-(4-methoxyphenyl)sulfanylacetate

HRID 2422213Notes

Reaction equation

HRID 2422213 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.C(N(CC)CC)C.O1CCCC1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 127654-Methoxybenzenethiol

Product 1

HCID 1482371Ethyl 2-(4-methoxyphenyl)sulfanylacetateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled mixture of 4-methoxythiophenol (15 g, 0.11 mol), triethylamine (28 mL, 0.20 mol) and tetrahydrofuran (150 mL) was added ethyl bromoacetate (21 g, 0.13 mol), and the mixture was stirred overnight at room temperature. Ethanol (10 mL) was added, the solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1) to give title compound (22 g, yield 92%). oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-42d83b6449764e33977a6b0946c3f50d
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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