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

HRID 745995

Reaction equation

HRID 745995 reaction equation
[Br:1][CH2:2][CH:3]1[O:5][CH2:4]1.CO.C(N(CC)CC)C.[C:15]([C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>C(OCC)C>[Br:1][CH2:2][CH:3]([OH:5])[CH2:4][S:25][C:22]1[CH:23]=[CH:24][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 754544-Tert-ButylbenzenethiolHCID 22728368Triethylamine methanol

Product 1

HCID 233113041-Bromo-3-(4'-tert-butylphenylthio)-propan-2-olYield 92.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 75.3 g [46.7 ml (0.55 mole)] 1-bromo-2,3-epoxypropane (epibromohydrin) in 14 ml 1:1 methanol/triethylamine cooled to 0°-5° C. in an ice-water bath, 83 g (0.5 mole) p-tert-butyl-thiophenol was added dropwise. After the addition was complete, the reaction mixture was allowed to come to room temperature and was stirred at room temperature for about 2 hours. The reaction mixture was dissolved in ethyl ether; washed with 1N sodium hydroxide, with 2N hydrochloric acid, with water until neutral and then with brine (twice). The organic phase was dried, filtered and concentrated to give 140.6 g of the above-identified product as an orange-red oil.

Workup

  1. additionAfter the addition
  2. customto come to room temperature
  3. washwashed with 1N sodium hydroxide, with 2N hydrochloric acid, with water until neutral and then with brine (twice)
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-51507bba8cc441238c9b44c7248546b8
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Linked notes

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