1-Chloroethyl phenyl carbonate → 1-Bromoethyl phenyl carbonate

HRID 1590336Notes

Reaction equation

HRID 1590336 reaction equation
[C:1](=[O:13])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:2][CH:3](Cl)[CH3:4].[Br-:14].C[SiH](C)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1](=[O:13])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:2][CH:3]([Br:14])[CH3:4]

Participants

4

Reactant 2

HCID 135570931-Chloroethyl phenyl carbonateHCID 131717854Trimethylsilane bromide

Product 1

HCID 136684321-Bromoethyl phenyl carbonate

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
90 °C

Procedure

15.4 g (0.077 mol) of 1-chloroethyl phenyl carbonate, 0.44 g (0.0014 mol) of tetrabutylammonium bromide and 13.7 g (0.090 mol) of trimethylsilane bromide are introduced into a distillation apparatus equipped with a 15 cm Vigreux column, a thermometer and a stirrer. The mixture is heated at 90° C. for 24 h and the trimethylsilane chloride released is removed by distillation. The product expected is then distilled. 17.2 g (Yld=91%) are obtained.

Workup

  1. customequipped with a 15 cm Vigreux column
  2. customthe trimethylsilane chloride released is removed by distillation
  3. distillationThe product expected is then distilled
  4. custom17.2 g (Yld=91%) are obtained

Sources & evidence

ORD record
ord-2aae454634124947b46ffea7650bbdb3
Source dataset
uspto-grants-1993_04
Patent number
US05202454

Reaction notes

Loading…