Iodine → 3-[2-Bromo-5-(methylsulfanyl)phenyl]propan-1-ol

HRID 1414213Notes

Reaction equation

HRID 1414213 reaction equation
[Mg].II.[Br:4][C:5]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][C:6]=1[CH2:7]Br.[CH3:15][CH2:16][O:17]CC>>[Br:4][C:5]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][C:6]=1[CH2:7][CH2:15][CH2:16][OH:17]

Participants

5

Reactant 4

HCID 807IodineHCID 3283Diethyl Ether2×HCID 5462224MagnesiumHCID 194371351-Bromo-2-(bromomethyl)-4-(methylsulfanyl)benzene

Product 1

HCID 214867593-[2-Bromo-5-(methylsulfanyl)phenyl]propan-1-ol

Procedure

To a suspension of 25.0 g of magnesium ribbon in a solution of 0.5 g of iodine in 550 ml of anhydrous ether is added 5 ml of a solution of 296.0 g of 2-bromo-5-(methylthio)benzyl bromide in 250 ml of anhydrous ether. The reaction is initiated by gentle heating, and the remainder of the solution is then added dropwise so as to maintain a reflux. Subsequently, the mixture is heated and stirred under reflux for 1 hour, and then cooled to 10°. A stream of nitrogen gas that has been bubbled through a reservoir containing 48.0 g of ethylene oxide is introduced into the reaction mixture. The addition of the ethylene oxide requires two hours. The mixture is subsequently stirred as it warms to room temperature, is stirred for 4 hours at room temperature, and then hydrolyzed by pouring on a mixture of 1 kg of ice and 55.0 g of ammonium chloride. Extraction with ether, followed by conventional workup of the ether solution, yield 210.0 g of 3 -(2-bromo-5-(methylthio)phenyl)-1-propanol, bp, about 125°-127° (0.6mm).

Workup

  1. additionthe remainder of the solution is then added dropwise so as
  2. temperatureto maintain a reflux
  3. temperatureSubsequently, the mixture is heated
  4. temperatureunder reflux for 1 hour
  5. temperaturecooled to 10°
  6. customA stream of nitrogen gas that has been bubbled through a reservoir
  7. additioncontaining 48.0 g of ethylene oxide
  8. additionis introduced into the reaction mixture
  9. additionThe addition of the ethylene oxide
  10. stirringThe mixture is subsequently stirred as it
  11. customwarms to room temperature
  12. stirringis stirred for 4 hours at room temperature
  13. additionhydrolyzed by pouring on a mixture of 1 kg of ice and 55.0 g of ammonium chloride
  14. extractionExtraction with ether
  15. customfollowed by conventional workup of the ether solution, yield 210.0 g of 3 -(2-bromo-5-(methylthio)phenyl)-1-propanol, bp, about 125°-127° (0.6mm)

Sources & evidence

ORD record
ord-123a2dd043a446728d64381ce1a5a381
Source dataset
uspto-grants-1977_01
Patent number
US04001233

Reaction notes

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