HCID 58526392, compound → HCID 58526348, compound

HRID 1470904Notes

Reaction equation

HRID 1470904 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=3)O[CH2:11]2)=[CH:4][CH:3]=1>ClC1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[CH2:8][CH2:9][CH:10]3[CH:11]([C:4]=2[CH:3]=1)[C:16]1[CH:17]=[C:18]([Br:21])[CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13]3

Participants

4

Reactant 1

HCID 58526392HCID 58526392, compound

Product 1

HCID 58526348HCID 58526348, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

37 ml (337 mmol) of titanium tetrachloride are added dropwise to a solution of 48 g (118 mmol) of 1,1-di-(p-bromophenylethyl)epoxyethane in 250 ml of chlorobenzene, and the mixture is stirred at 80° C. for 18 h. The reaction mixture is carefully poured into 100 ml of ice-water, the phases are separated, and the aqueous phase is extracted three times with 70 ml of chloroform. The combined organic phases are washed with 100 ml of saturated NaCl solution and 100 ml of NaHCO3 solution and dried over sodium sulfate, the solvent is stripped off, and the residue is recrystallised from ethanol. Yield: 43 g (110 mmol), 94%.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with 70 ml of chloroform
  3. washThe combined organic phases are washed with 100 ml of saturated NaCl solution and 100 ml of NaHCO3 solution
  4. dry with materialdried over sodium sulfate
  5. customthe residue is recrystallised from ethanol

Sources & evidence

ORD record
ord-50352123b35c4da2a9452f9caaf93bf8
Source dataset
uspto-grants-2015_04
Patent number
US09006503B2

Reaction notes

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