Water → 485814-90-2

HRID 1272280Notes

Reaction equation

HRID 1272280 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[CH:10][C:7]=1[CH:8]=[O:9].[Br:16]Br.O>C(Cl)Cl>[Br:16][C:13]1[C:6]([CH3:5])=[C:7]([CH:10]=[C:11]([CH3:15])[C:12]=1[CH3:14])[CH:8]=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 22013Duryl aldehydeHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23113828485814-90-2Yield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum chloride (48.0 g, 360 mmol) was added to a solution of 2,4,5-trimethylbenzaldehyde (21.3 g, 144 mmol) in methylene chloride (200 ml) under ice cooling and the mixture was allowed to warm to room temperature. To the mixture was added dropwise bromine (7.80 ml, 151 mmol) at room temperature. The mixture was stirred for 4 hours, poured into water. Methylene chloride was removed under reduced pressure. The residue was extracted with ethyl acetate, and the organic extract was washed with water, saturated aqueous sodium bicarbonate, 5% aqueous sodium sulfite, water and saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 32.5 g (yield 100%) of the title compound. mp. 108–110° C.

Workup

  1. customMethylene chloride was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with water, saturated aqueous sodium bicarbonate, 5% aqueous sodium sulfite, water and saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-50adb22046bf44e3bf95fc3f5b7723f5
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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