Water → 2-benzoyl-5-chlorobenzofuran

HRID 1402919Notes

Reaction equation

HRID 1402919 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[CH2:11](Br)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].O>C(O)C>[C:12]([C:11]1[O:10][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=1)(=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 40202632-benzoyl-5-chlorobenzofuranYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-2-hydroxybenzaldehyde (2 g) and phenacyl bromide (1.85 g) in ethanol (10 ml) potassium carbonate (3.53 g) was added. The mixture was stirred at 80° C. for 1 h. Then the reaction mixture was poured into water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 12:1) to give 2-benzoyl-5-chlorobenzofuran (1.85 g) as colourless solid.

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by flash chromatography on silica gel (hexane/ethyl acetate 12:1)

Sources & evidence

ORD record
ord-fff25e4fc43a44a3a51b021cae092819
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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