M-Xylene → HCID 12195664, compound

HRID 1925194Notes

Reaction equation

HRID 1925194 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 mL, 3-neck rounded bottom flask equipped with a magnetic stirring bar and a reflux condenser, was filled with nitrogen atmosphere and charged with 71.16 g of AlCl3 (0.53 mol, 2.3 eq.) dissolved in 240 mL of chlorobenzene. At room temperature 28.38 mL of m-xylene (0.23 mol, 1 eq.) 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, 1 eq.) 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 r.t. and stirred for 2 hours. Then it was transferred into a flask containing a solution of ice/HCl 37%=3/1. The organic phase was extracted with Et2O (3×200 mL): the combined organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. An orange oil was obtained as product (37.48 g, yield 93.5%). The latter was used as such without further purification in the next step.

Workup

  1. customA 500 mL, 3-neck rounded bottom flask equipped with a magnetic stirring bar and a reflux condenser
  2. additionwas filled with nitrogen atmosphere
  3. customobtaining a light yellow suspension
  4. additionAt the end of the addition a dark-red slurry
  5. customwas obtained
  6. temperatureto warm up to r.t.
  7. customThen it was transferred into a flask
  8. extractionThe organic phase was extracted with Et2O (3×200 mL)
  9. dry with materialthe combined organic phases were dried over Na2SO4
  10. filtrationfiltered
  11. customthe solvent was removed in vacuo
  12. customAn orange oil was obtained as product (37.48 g, yield 93.5%)
  13. customsuch without further purification in the next step

Sources & evidence

ORD record
ord-9df1b95b396c4921a9cc2d2405863209
Source dataset
uspto-grants-2012_05
Patent number
US08178636B2

Reaction notes

Loading…