Ethyl bromo(4-methoxyphenyl)acetate → HCID 14743212, compound

HRID 393171Notes

Reaction equation

HRID 393171 reaction equation
[Na].[SH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.Br[CH:15]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:19]([O:18][C:16]([CH:15]([S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 131740Ethyl bromo(4-methoxyphenyl)acetateHCID 5360545SodiumHCID 12738999HCID 12738999, compound

Product 1

HCID 14743212HCID 14743212, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of sodium (0.46 g, 0.02 g-atom) in 25 mL of anhydrous ethanol, a solution of 1-(2-mercaptophenyl)pyrrole (3.5 g, 0.02 mol) in 8 mL of anhydrous ethanol was added dropwise and the mixture was allowed to stirr for 1 h. After evaporation of the solvent the residue was dissolved in anhydrous tetrahydrofuran (25 mL) and ethyl α-bromo-p-methoxyphenylacetate (5.5 g, 0.02 mol) was slowly added. The reaction mixture was heated at 60° C. for 5 h and then was cooled and poured onto crushed ice, extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was purified by flash chromatography (dichloromethane as eluant) giving 5.05 g (69%) of the desired product. IR (neat) 1735 cm−1; 1HNMR (CDCl3) δ 1.06 (t, 3 H), 3.76 (s, 3 H), 4.07 (q, 2 H), 4.30 (s, 1 H), 6.35 (t, 2 H), 6.70-7.70 (m, 10 H).

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in anhydrous tetrahydrofuran (25 mL)
  3. temperaturewas cooled
  4. additionpoured
  5. customonto crushed ice
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography (dichloromethane as eluant)

Sources & evidence

ORD record
ord-ffe5ba99a27d42b9a5df416efef81db6
Source dataset
uspto-grants-2004_10
Patent number
US06806267B1

Reaction notes

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