1,3-Dibromo-2-propanol → 1,3-Bis(benzylthio)-2-propanol

HRID 259273Notes

Reaction equation

HRID 259273 reaction equation
Br[CH2:2][CH:3]([OH:6])[CH2:4]Br.[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[H-].[Na+]>O1CCCC1>[CH2:7]([S:14][CH2:2][CH:3]([OH:6])[CH2:4][S:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 72871,3-Dibromo-2-propanolHCID 7509Benzyl mercaptanHCID 24758Sodium hydride

Product 1

HCID 158896411,3-Bis(benzylthio)-2-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,3-dibromo-2-propanol (2.18 g.) is added to a stirred suspension of the salt obtained by mixing 2.7 g. benzyl mercaptan and sodium hydride (56% dispersion in mineral oil; 900 mg.) in 50 ml. dry tetrahydrofuran. After 2 hours at room temperature, the solvent is removed and 20 ml. of water is added to the residue. The resultant aqueous mixture is extracted with ether and the extracts washed with water, dried over magnesium sulfate and evaporated to yield 1,3-bis(benzylthio)-2-propanol.

Workup

  1. customobtained
  2. additionby mixing 2.7 g
  3. customthe solvent is removed
  4. additionof water is added to the residue
  5. extractionThe resultant aqueous mixture is extracted with ether
  6. washthe extracts washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-536ea60cb1c54306a8415c4d5b8a0e4e
Source dataset
uspto-grants-1977_07
Patent number
US04036970

Reaction notes

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