Water → HCID 22731331, compound

HRID 2085571Notes

Reaction equation

HRID 2085571 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]=2[CH:20]=1.O>ClCCl>[C:5]([C:12]1[C:13]2[O:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]=2[CH:20]=[C:10]([Br:9])[CH:11]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 53235955-Bromo-3,3-dimethyl-2,3-dihydro-1-benzofuran2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 22731331HCID 22731331, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred, cooled (ice-bath) suspension of aluminum chloride (0.25 g, 1.7 mmol) in 3 mL of anhydrous dichloromethane was treated with acetyl chloride (0.2 mL, 2.6 mmol) under argon. A solution of 5-bromo-3,3-dimethyl-2,3-dihydro-benzofuran (Intermediate 2, 0.22 g) in 1.5 mL of anhydrous dichloromethane was cannulated into the clear solution, and the resulting deep red solution was allowed to warm to ambient temperature over 1 h. The reaction mixture was poured onto iced water and extracted with dichloromethane. The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to a dirty white solid. Flash column chromatography on silica gel (230-400 mesh) using 6% ethyl acetate in hexane as the eluent afforded the title compound as a white solid (0.177 g, 67%).

Workup

  1. temperatureA stirred, cooled
  2. extractionextracted with dichloromethane
  3. extractionThe combined organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a dirty white solid

Sources & evidence

ORD record
ord-f757073b3f074a82b55ff57ffeb5488a
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

Loading…