Epibromohydrin → 1-Bromo-3-(4'-tert-butylphenylthio)-propan-2-ol

HRID 745994

Reaction equation

HRID 745994 reaction equation
[Br:1][CH2:2][CH:3]1[O:5][CH2:4]1.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>CO.C(N(CC)CC)C>[Br:1][CH2:2][CH:3]([OH:5])[CH2:4][S:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 18430EpibromohydrinHCID 754544-Tert-Butylbenzenethiol

Product 1

HCID 233113041-Bromo-3-(4'-tert-butylphenylthio)-propan-2-olYield 102.5%

Reagents, catalysts & solvents 1

HCID 22728368Triethylamine methanolSolvent

Procedure

To a stirred solution of 64.9 ml [103.67 g (0.758 mole)] 1-bromo-2,3-epoxypropane dissolved in 18 ml methanol/triethylamine (1:1) cooled to 5°-10° C. in a water-ice bath, 124.5 g (0.75 mole) p-tert-butylthiophenol was added dropwise. After the addition was complete (about 21/4 hours), the reaction mixture was allowed to come to room temperature and was allowed to stir at room temperature for about 2 hours. Volatiles were removed in vacuo to give 233.1 g of crude product as a viscous oil.

Workup

  1. temperaturecooled to 5°-10° C. in a water-ice bath
  2. additionAfter the addition
  3. custom(about 21/4 hours)
  4. customto come to room temperature
  5. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-50ead1572416481d8832122eb3a19d4c
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Linked notes

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