2-Acetylfuran → 2-Bromo-1-(furan-2-yl)ethan-1-one

HRID 622177Notes

Reaction equation

HRID 622177 reaction equation
[Br:1]Br.[C:3]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)(=[O:5])[CH3:4].O1CCOCC1>C(Cl)(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 145052-AcetylfuranHCID 24408BromineHCID 312751,4-Dioxane

Product 1

HCID 27950762-Bromo-1-(furan-2-yl)ethan-1-oneYield 94.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (71.14 ml, 1.39 mol) is added dropwise over 1 hour to a solution of 117.59 g (1.07 mol) of 2-acetylfuran (1) in a mixture of 900 ml of either and 400 ml of 1,4-dioxane, at 0° C. under a nitrogen atmosphere. The reaction is warmed to ambient temperature and stirred for 18 hours, then quenched with 1.1 liter of saturated aqueous ammonium chloride and extracted with chloroform. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a dark oil. Flash-chromatography on neutral silica gel using chloroform as eluent followed by distillation using a Kugelruhr apparatus gives 190.81 g (94%) of compound 2 as a light yellow oil, boiling point 85° C. (0.30 mmHg).

Workup

  1. customat 0° C.
  2. customquenched with 1.1 liter of saturated aqueous ammonium chloride
  3. extractionextracted with chloroform
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a dark oil
  7. distillationfollowed by distillation

Sources & evidence

ORD record
ord-68a79839027a49d780b21fe087d77f21
Source dataset
uspto-grants-1988_09
Patent number
US04769469

Reaction notes

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