Ethyl Bromide → HCID 20470474, compound

HRID 1388801Notes

Reaction equation

HRID 1388801 reaction equation
C(Br)C.[Mg].Cl[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([CH3:15])=[CH2:14])=[CH:8][CH:7]=1.Br[CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].[Cl-].[NH4+]>[Ni](Cl)Cl.C1COCC1>[CH3:15][C:13](=[CH2:14])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 79040Ethyl 2-bromopropionateHCID 89985Benzene, 1-chloro-4-(2-methyl-2-propenyl)-HCID 5462224Magnesium

Product 1

HCID 20470474HCID 20470474, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 8028TetrahydrofuranSolvent5×

Conditions

Temperature
130 °C

Procedure

Under a nitrogen atmosphere, 5 ml of dry THF and 0.3 ml of ethyl bromide were added to 2.92 g of magnesium turnings for Grignard reaction, and the mixture was stirred. Heat was generated and the temperature of the mixture rose. Then, a solution composed of 16.65 g of p-chloro-(2-methyl-2-propenyl)benzene and 2 ml of THF was added dropwise, and the temperature of the mixture was raised to 130° C. Some amount of THF was added, and the mixture was heated under reflux at 100° C. for 4 hours. After cooling, 60 ml of THF was added, and the resulting reaction mixture was added dropwise to a solution composed of 18.1 g of ethyl α-bromopropionate, 0.065 g of nickel chloride and 40 ml of THF. After the addition, the mixture was stirred for 1 hour, and an aqueous solution of ammonium chloride was added. The mixture was extracted with diethyl ether. The ethereal extract was washed with an aqueous solution of sodium chloride, dried, concentrated and distilled to give 11.3 g (yield 48.7%) of ethyl α-[p-(2-methyl-2-propenyl)phenyl]propionate having the following properties.

Workup

  1. temperatureHeat
  2. additionwas added dropwise
  3. temperaturethe mixture was heated
  4. temperatureunder reflux at 100° C. for 4 hours
  5. temperatureAfter cooling
  6. customthe resulting reaction mixture
  7. additionwas added dropwise to a solution
  8. additionAfter the addition
  9. stirringthe mixture was stirred for 1 hour
  10. extractionThe mixture was extracted with diethyl ether
  11. extractionThe ethereal extract
  12. washwas washed with an aqueous solution of sodium chloride
  13. customdried
  14. concentrationconcentrated
  15. distillationdistilled

Sources & evidence

ORD record
ord-66c58ce799504d10aa2aad995d793871
Source dataset
uspto-grants-1984_02
Patent number
US04433160

Reaction notes

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