Chlorosuccinimide → HCID 21838338, compound

HRID 1740293Notes

Reaction equation

HRID 1740293 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:2]1.[Cl:16]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:16][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 21838025Benzoic acid, 3-(3-furanyl)-, methyl ester

Product 1

HCID 21838338HCID 21838338, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of methyl 3-(furan-3-yl)benzoate (1.0 g) in acetic acid (5 ml) was stirred at 110° C., and to this was slowly added N-chlorosuccinimide (0.66 g). The mixture was heated at 110° C. for 1.5 hours and then cooled to room temperature. The reaction mixture was poured onto water and the product was extracted with ethyl acetate, washed successively with water, hydrochloric acid, and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane:toluene (2:1) to afford methyl 3-(2-chlorofuran-3-yl)benzoate (0.24 g).

Workup

  1. temperaturecooled to room temperature
  2. additionThe reaction mixture was poured onto water
  3. extractionthe product was extracted with ethyl acetate
  4. washwashed successively with water, hydrochloric acid, and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane:toluene (2:1)

Sources & evidence

ORD record
ord-4aec4b9b4105435e840289afc68639ef
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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