Aluminum(III) Chloride → HCID 22172947, compound

HRID 716455Notes

Reaction equation

HRID 716455 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][CH:13]([CH3:17])[C:14](Cl)=[O:15])[CH:11]=1>ClCCl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH3:18])=[C:10]2[C:11]=1[C:14](=[O:15])[CH:13]([CH3:17])[CH2:12]2

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 89392410HCID 89392410, compound

Product 1

HCID 22172947HCID 22172947, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 49.5 g (0.371 mol, 1.2 eq.) of AlCl3 in 300 ml of dichloromethane a solution of 85.3 g (0.310 mol) of 3-(5-bromo-2-methylphenyl)-2-methylpropanoyl chloride in 50 ml of dichloromethane was added dropwise. This mixture was stirred overnight at room temperature and then poured on 500 g of ice. The organic layer was separated, and the aqueous layer was additionally extracted with 3×75 ml of dichloromethane. The combined organic extract was washed by aqueous K2CO3, dried over K2CO3, passed through a short pad of silica gel, and then evaporated to dryness. This procedure gave 74.0 g (>99%) of 7-bromo-2,4-dimethylindan-1-one as a light-orange liquid, solidified at room temperature, which was further used without an additional purification.

Workup

  1. additionwas added dropwise
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was additionally extracted with 3×75 ml of dichloromethane
  4. extractionThe combined organic extract
  5. washwas washed by aqueous K2CO3
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-48aa8145633b4c919197a4210979fdaa
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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