Potassium Acetate → HCID 13243422, compound

HRID 2295854Notes

Reaction equation

HRID 2295854 reaction equation
[Br:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Br)[CH:8]=2)=[CH:5][CH:6]=1.[C:15]([O-:18])(=[O:17])[CH3:16].[K+]>C(O)(=O)C.O>[C:15]([O:18][CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:4]2[O:3][C:2]([Br:1])=[CH:6][CH:5]=2)[CH:8]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 132459292-Bromo-5-[3-(bromomethyl)phenyl]furan

Product 1

HCID 13243422HCID 13243422, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A stirred solution of 7.3 g (0.023 mol) of 2-bromo-5-(3-bromomethylphenyl)furan in 50 mL of acetic acid was cooled in an ice-water bath, and 3.4 g (0.035 mol) of potassium acetate was added. Upon complete addition, the reaction mixture was heated to reflux temperature and stirred for 19 hours. The reaction mixture was transferred to a separatory funnel, diluted with 100 mL of water, then extracted with two portions of 150 mL each of chloroform. The combined extracts were washed with one portion of 150 mL of a saturated aqueous solution of sodium chloride, two portions of 150 mL each of a saturated aqueous solution of sodium bicarbonate, and finally with one portion of 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to column chromatography on silica gel, eluting with hexane: chloroform (2:1). The appropriate fractions were combined to give 3.8 g of 3-(2-bromo-5-furanyl)phenylmethyl acetate.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux temperature
  4. customThe reaction mixture was transferred to a separatory funnel
  5. extractionextracted with two portions of 150 mL each of chloroform
  6. washThe combined extracts were washed with one portion of 150 mL of a saturated aqueous solution of sodium chloride, two portions of 150 mL each of a saturated aqueous solution of sodium bicarbonate
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure
  10. customto give a residual oil
  11. washeluting with hexane: chloroform (2:1)

Sources & evidence

ORD record
ord-852b08049f094f358bb25b690afe94cd
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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