Water → 1-(5-Bromofuran-2-yl)ethan-1-one

HRID 1965868Notes

Reaction equation

HRID 1965868 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=[O:3])[CH3:2].[Br:9]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:9][C:6]1[O:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 145052-AcetylfuranHCID 67184N-bromobutanimide

Product 1

HCID 110305851-(5-Bromofuran-2-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a one-neck-flask charged with 2-acetylfuran (5.51 g, 50 mmol) in DMF (40 ml) at 0° C., was added N-Bromosuccinimide (9.79 g, 55.0 mmol) portionwise with stirring. The reaction mixture was stirred at rt overnight. The reaction mixture was poured into water (400 mL), extracted with ether (150 mL×3). The combined organic layers was dried, concentrated and purified on a silica gel column (Hexanes:EtOAc=4:1) to afford a white solid GC-4-89 (3 g, 31.7%). 1H-NMR (400 MHz, CDCl3) δ: 7.12 (d, J=3.6 Hz, 1H), 6.49 (d, J=3.2 Hz, 1H), 2.46 (s, 3H)

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. extractionextracted with ether (150 mL×3)
  3. customThe combined organic layers was dried
  4. concentrationconcentrated
  5. custompurified on a silica gel column (Hexanes:EtOAc=4:1)
  6. customto afford a white solid GC-4-89 (3 g, 31.7%)

Sources & evidence

ORD record
ord-6be7e02a8ca448c690637a2381b2bf9d
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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