Thiophenol → HCID 13425461, compound

HRID 745993Notes

Reaction equation

HRID 745993 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH:10]1[O:12][CH2:11]1.C(N(CC)CC)C>CO>[Br:8][CH2:9][CH:10]([OH:12])[CH2:11][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 18430Epibromohydrin

Product 1

HCID 13425461HCID 13425461, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thiophenol, 11.0 g (0.10 mole), was added dropwise over a period of one hour, to a cold (0° C.) mixture of 13.69 g [8.5 ml (0.1 mole)] 1-bromo-2,3-epoxypropane (epibromohydrin), 1.5 ml [1.09 g (0.02 moles)] triethylamine and 1.5 ml methanol. The reaction mixture was then allowed to come to room temperature and was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in ether, washed several times with water and once with brine. The organic phase was dried over magnesium sulfate, filtered and concentrated to give 22.7 g of the above-identified product as an amber oil.

Workup

  1. customto come to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed several times with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b78660d3255b4646909b5fbb26c1d9b9
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Reaction notes

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