Water → 485814-90-2

HRID 2376289Notes

Reaction equation

HRID 2376289 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:7]([CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[Br:16]Br.O>ClCCl>[Br:16][C:9]1[C:2]([CH3:1])=[C:3]([CH:6]=[C:7]([CH3:11])[C:8]=1[CH3:10])[CH:4]=[O:5]

Participants

6

Reactant 4

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

Product 1

HCID 23113828485814-90-2Yield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,4,5-trimethylbenzaldehyde (21.3 g, 144 mmol) in dichloromethane (200 mL) was added aluminum chloride (48.0 g, 360 mmol) with ice-cooling, and the mixture was warmed to room temperature. Bromine (7.80 mL, 151 mmol) was added dropwised to the reaction solution at room temperature, the mixture was stirred for 4 hours, water was added to the reaction solution, and dichloromethane was distilled off under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was washed with water, a saturated sodium hydrogen carbonate solution, 5% sodium sulfite aqueous solution, water and a saturated brine. The organic layer was dried over anhydrous sodium sulfate and then was concentrated under reduced pressure to obtain 32.5 g (yield 100%) of the title compound. Melting point: 108-110° C.

Workup

  1. temperaturecooling
  2. customdropwised to the reaction solution at room temperature
  3. distillationwas distilled off under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f34114439ba4a8aa4f1cf9822e10568
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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