4-Ethylbenzoyl chloride → HCID 21978150, compound

HRID 1454773Notes

Reaction equation

HRID 1454773 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH2:15]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)[CH3:16].C(=O)(O)[O-].[Na+]>ClCCl>[Br:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:21]([C:20]1[CH:24]=[CH:25][C:17]([CH2:15][CH3:16])=[CH:18][CH:19]=1)=[O:22])=[CH:9][NH:10]2

Participants

6

Reactant 4

HCID 853684-Ethylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 6764944-BromoindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21978150HCID 21978150, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of AlCl3 (3.0 g, 22.5 mmol) in dichloromethane (50 mL) was added a solution of 4-bromoindole (2.21 g, 11.3 mmol) in dichloromethane (25 mL) at room temperature over the period of 20 mins, followed by the addition of a solution of 4-ethyl-benzoyl chloride (2.5 mL, 17 mmol) in dichloromethane (25 mL) over the period of 20 mins. The resulting solution was stirred at room temperature overnight, and saturated sodium bicarbonate solution was added in a water-ice bath to quench the reaction. The aqueous layer was extracted with dichloromethane. The organics were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was triturated in diethyl ether to obtain the title compound (1.8 g, 48%) as white solids.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated in diethyl ether

Sources & evidence

ORD record
ord-4628785d3bbc4c5fb2d669d537e3254e
Source dataset
uspto-grants-2009_01
Patent number
US07482330B2

Reaction notes

Loading…