M-Xylene → HCID 12195664, compound

HRID 2425304Notes

Reaction equation

HRID 2425304 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([CH3:12])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.Br[C:14]([CH3:19])([CH3:18])[C:15](Br)=[O:16]>ClC1C=CC=CC=1>[CH3:18][CH:14]1[CH2:19][C:8]2[C:9](=[CH:10][C:5]([CH3:12])=[CH:6][C:7]=2[CH3:11])[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 7929M-XyleneHCID 886852-Bromo-2-methylpropionyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12195664HCID 12195664, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

A 500 μL, 3-neck rounded bottom flask equipped with a magnetic stirring bar and a reflux condenser, was charged under nitrogen with 71.16 g of AlCl3 (0.53 mol) dissolved in 240 mL of chlorobenzene. At room temperature 28.38 mL of m-xylene (0.23 mol) were added dropwise obtaining a light yellow suspension. The flask was then cooled to 0° C. and 28.68 mL of 2-bromoisobutyryl bromide (0.23 mol) were slowly added. At the end of the addition a dark-red slurry was obtained. The reaction mixture was then allowed to warm up to room temperature (r.t.) and stirred for 2 hours. Then it was transferred into a flask containing a solution of 3/1 ice/37% HCl. The organic phase was extracted with Et2O (3×200 mL), the combined organic phases were dried over Na2SO4, filtered and the solvents were removed in vacuo to leave 37.48 g of an orange oil (yield 93.5%). The latter was used as such in the next step without further purification.

Workup

  1. customA 500 μL, 3-neck rounded bottom flask equipped with a magnetic stirring bar and a reflux condenser
  2. customobtaining a light yellow suspension
  3. additionAt the end of the addition a dark-red slurry
  4. customwas obtained
  5. temperatureto warm up to room temperature (r.t.)
  6. customThen it was transferred into a flask
  7. extractionThe organic phase was extracted with Et2O (3×200 mL)
  8. dry with materialthe combined organic phases were dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-0a639c07c2fb4bb3b69193bb58cbd87d
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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