Hydrochloric Acid → HCID 13269113, compound

HRID 1648753Notes

Reaction equation

HRID 1648753 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1([Mg]Br)C=CC=CC=1.[Cl:17][C:18]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:19]=1[C:20](=[O:23])[CH2:21][Cl:22].Cl>CCOCC>[C:3]1([C:20]([C:19]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:18]=2[Cl:17])([OH:23])[CH2:21][Cl:22])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 202502,2',4'-TrichloroacetophenoneHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 13269113HCID 13269113, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

Into a 1 liter three-necked flask are placed 5.35 g (0.22 m) of magnesium turning and 50 ml of anhydrous ether. Bromobenzene (34.5 g, 0.22 m) in 100 ml of ether is then added dropwise under nitrogen. When the reaction started, the rate of addition is controlled so that ether remained refluxing gently. After the addition, the mixture is stirred for 10 minutes at room temperature and then cooled to 10° with an ice bath. To this phenyl magnesium bromide solution is added 44.7 g (0.2 m) of 2,4-dichlorophenacyl chloride dissolved in 100 ml of ether dropwise. The reaction mixture is stirred at room temperature for 1/2 hour followed by slow addition of dilute HCl solution (300 ml). The phases are then separated and the ether layer is washed with saturated sodium bicarbonate solution and dried over MgSO4. Solvent is evaporated to give 56 g of a yellow oil. Vacuum distillation (156°/0.1 mm) affords 40 g of pure product.

Workup

  1. customInto a 1 liter three-necked flask are placed
  2. additionthe rate of addition
  3. temperatureremained refluxing gently
  4. additionAfter the addition
  5. temperaturecooled to 10° with an ice bath
  6. stirringThe reaction mixture is stirred at room temperature for 1/2 hour
  7. customThe phases are then separated
  8. washthe ether layer is washed with saturated sodium bicarbonate solution
  9. dry with materialdried over MgSO4
  10. customSolvent is evaporated

Sources & evidence

ORD record
ord-306fba941015426c8210b75f94366a04
Source dataset
uspto-grants-1983_11
Patent number
US04413003

Reaction notes

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