Water → 1-(5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-ethanone

HRID 2290147Notes

Reaction equation

HRID 2290147 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Br:9][C:10]1[C:11]([CH3:21])=[CH:12][C:13]2[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[C:14]=2[CH:20]=1.O>ClCCl>[Br:9][C:10]1[C:11]([CH3:21])=[C:12]([C:5](=[O:7])[CH3:6])[C:13]2[O:17][CH2:16][C:15]([CH3:18])([CH3:19])[C:14]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18699201HCID 18699201, compound

Product 1

HCID 186991761-(5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-ethanoneYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred, cooled (ice-bath) suspension of aluminum chloride (6.85 g, 51.4 mmol) in 50 mL of anhydrous dichloromethane was treated with acetyl chloride (3.7 mL, 51.4 mmol) under argon. A solution of 5-bromo-3,3,3-trimethyl-2,3-dihydro-benzofuran (Compound 47, 5.2 5 g, 25.7 mmol)in 10 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 hour. 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 using 6% ethyl acetate in hexane as the eluent afforded the title compound (4.5 g, 61.6%). 1H NMR (300 MHz, CDCl3): δ 7.30 (s, 1H), 4.28 (s, 2H), 2.56 (s, 3H), 2.34 (s, 3H), 1.33 (s, 6H).

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-f1bedb5ba8704a06b6f2eaf9fc629535
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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