Acetic Acid → HCID 67069079, compound

HRID 604744Notes

Reaction equation

HRID 604744 reaction equation
[Br:1]Br.C(O)(=O)C.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[C:11]([CH3:23])[CH:10]=1>O>[Br:1][C:14]1[CH:13]=[C:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:11]([CH3:23])=[CH:10][C:9]=1[O:8][CH3:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 67069117HCID 67069117, compound

Product 1

HCID 67069079HCID 67069079, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Br2 was added dropwise to an acetic acid (35 mL) solution of 4-methoxy-2-methyl-1-(4-methylbenzyl)benzene while cooled on ice. The reaction mixture was stirred at 110° C. for two hours. After the reaction mixture was added with water while cooled on ice and extracted with ethyl acetate, the organic phase was washed with a saturated sodium bicarbonate aqueous solution and brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to obtain a yellow oily title compound (4.21 g, 80%).

Workup

  1. temperaturewhile cooled on ice
  2. temperaturewhile cooled on ice
  3. extractionextracted with ethyl acetate
  4. washthe organic phase was washed with a saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. customthe residue obtained
  8. customby evaporating the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-2195d1fca31e4908b5d46166c0f52ab0
Source dataset
uspto-grants-2011_03
Patent number
US07910619B2

Reaction notes

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