Hydrochloric Acid → (r)-2-Phenyl-1-(4-iodophenyl)propane

HRID 2214320Notes

Reaction equation

HRID 2214320 reaction equation
[Mg].C(Br)C.[C:5]1([C@H:11]([CH3:20])[CH2:12][C:13]2[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I:21]I.Cl>O1CCCC1>[C:5]1([C@H:11]([CH3:20])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([I:21])=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 69111420(r)-2-Phenyl-1-(4-chlorophenyl)propane

Product 1

HCID 69111052(r)-2-Phenyl-1-(4-iodophenyl)propaneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent5×

Procedure

35 ml of tetrahydrofuran (THF) was added to 11.6 g (0.48 mol) of magnesium, and a solution having 23.6 g (0.22 mol) of ethyl bromide dissolved in 70 ml of THF was dropwise added thereto over a period of 1 hour at room temperature with stirring, followed by stirring for 1 hour. A solution having 50.0 g (0.22 mol) of (R)-2-phenyl-1-(4-chlorophenyl)propane dissolved in 50 ml of THF was dropwise added thereto over a period of 30 minutes at room temperature, followed by stirring under reflux for 5 hours. After the mixture was cooled to room temperature, 250 ml of THF was added thereto, and the mixture was further cooled to −30° C. A solution having 112 g (0.44 mol) of iodine dissolved in 300 ml of THF was dropwise added thereto at −30° C. over a period of 30 minutes, followed by stirring for 1 hour. The temperature was raised to 0° C., and 120 ml of 4M hydrochloric acid was dropwise added thereto, followed by stirring for 10 minutes. After extraction with toluene from the reaction liquid, washing with water and drying were carried out to obtain 69.8 g of (R)-2-phenyl-1-(4-iodophenyl)propane (GC purity: 95.2%, 0.22 mol).

Workup

  1. additionwas dropwise added
  2. stirringby stirring for 1 hour
  3. additionwas dropwise added
  4. waitover a period of 30 minutes at room temperature
  5. stirringby stirring
  6. temperatureunder reflux for 5 hours
  7. temperatureAfter the mixture was cooled to room temperature
  8. temperaturethe mixture was further cooled to −30° C
  9. additionwas dropwise added
  10. waitat −30° C. over a period of 30 minutes
  11. stirringby stirring for 1 hour
  12. temperatureThe temperature was raised to 0° C.
  13. stirringby stirring for 10 minutes
  14. extractionAfter extraction with toluene
  15. customfrom the reaction liquid
  16. washwashing with water
  17. customdrying

Sources & evidence

ORD record
ord-e45a4313e4b4493db2b4f8201aa1202d
Source dataset
uspto-grants-2006_09
Patent number
US07108895B2

Reaction notes

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