Water → 1-(5-Bromo-1-benzofuran-2-yl)ethan-1-one

HRID 1394577Notes

Reaction equation

HRID 1394577 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.Cl[CH2:12][C:13](=[O:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:13]([C:14]1[O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=1)(=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 10796Cesium carbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7056701-(5-Bromo-1-benzofuran-2-yl)ethan-1-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.0 g (24.9 mmol) of 5-bromo-salicylaldehyde, 3.0 g (32.3 mmol, 2.6 mL) of chloroacetone and 12 g (37.2 mmol) of Cs2CO3 in 30 mL of dry DMF was heated to 60° C. overnight. After cooling at room temperature, water (100 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was directly recrystallized from hexane to afford 4.14 g (17.3 mmol, yield: 70%) of 2-acetyl-5-bromo benzo[b]furan as a pale orange crystal. 1H NMR (CDCl3), δ: 7.84 (d, J=1.9 Hz, 1H), 7.56 (dd, J=9.0, 2.1 Hz, 1H), 7.45 (d, J=8.9 Hz, 1H), 7.42 (s, 1H), 2.60 (s, 3H).

Workup

  1. temperatureAfter cooling at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvents were removed under reduced pressure
  5. customThe crude product was directly recrystallized from hexane

Sources & evidence

ORD record
ord-f950c118c5d74ea5915f974821fdce07
Source dataset
uspto-grants-2008_03
Patent number
US07348359B2

Reaction notes

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