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

HRID 2113553Notes

Reaction equation

HRID 2113553 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-oneYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. The reaction mixture was stirred overnight, then poured onto cold water. The product was extracted with ether (200 mL, 3× times). Yield 61%, mp 92-93° C. (hexanes/ether, Lit. mp 94-95° C.; see Gilman H., et al., J. Am. Chem. Soc., 53, 4192-4196 (1931). 1H NMR (CDCl3); δ 2.45 (s, 3H), 6.49 (d, J=3.9 Hz, 1H), 7.12 (d, J=3.6 Hz, 1H). 13C NMR; δ 8185.4, 154.4, 128.2, 118.9,114.3, 25.7.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. extractionThe product was extracted with ether (200 mL, 3× times)

Sources & evidence

ORD record
ord-c271993d967744a1a8f5d8ffb28e360a
Source dataset
uspto-grants-2008_10
Patent number
US07432278B2

Reaction notes

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