Benzoyl chloride → (2-Ethyl-3-benzofuranyl)phenylmethanone

HRID 898348Notes

Reaction equation

HRID 898348 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)[CH3:2].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[C:7]=1[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 765822-Ethylbenzofuran

Product 1

HCID 12391264(2-Ethyl-3-benzofuranyl)phenylmethanoneYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirring solution of 2-ethyl benzofuran (43.8 g; 0.3 mol) in methylene chloride (300 mL) was cooled in an ice bath. Benzoyl chloride (42.2 g; 0.3 mol) was added. Tin (IV) chloride (85 g; 0.33 mol) was then added dropwise. The mixture was stirred at room temperature for 30 minutes then at reflux for one hour. The mixture was then cooled to room temperature, poured over ice, and extracted with ether. The ethereal extract was washed with brine, dried over anhydrous magnesium sulfate, and solvent evaporated. The residue was purified by flash chromatography on silica gel using 1% ethyl acetate in hexane as an eluent. The product was obtained as an oil (26 g). Mass spectrum (ESI, [M+] m/z 250. 1HNMR (400 MHz, DMSO-d6): δ 1.21 (t, 3H, J=7.47 Hz), 2.76 (q, 2H, J=7.47 Hz), 7.21 (dt, 1H, J=7.25, 1.1 Hz), 7.3-7.38 (m, 2H), 7.52-7.56 (m, 2H), 7.61-7.69 (m, 2H), 7.73-7.76 (m, 2H). Elemental Analysis for C17H14O2: Calculated: C, 81.58; H, 5.64. Found: C, 81.73; H, 5.56.

Workup

  1. temperatureat reflux for one hour
  2. temperatureThe mixture was then cooled to room temperature
  3. additionpoured over ice
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate, and solvent
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel using 1% ethyl acetate in hexane as an eluent

Sources & evidence

ORD record
ord-9456f17efb444314b8486dff5598092c
Source dataset
uspto-grants-2008_04
Patent number
US07351726B2

Reaction notes

Loading…