Thionyl Chloride → 2-bromooctanoyl Chloride

HRID 37538

Reaction equation

HRID 37538 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3](O)=[O:4].S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([Cl:14])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 552003Octanoic acid, 2-bromo-

Product 1

HCID 110756072-bromooctanoyl ChlorideYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 20 g (90 mmol) 2-bromooctanoic acid in 100 mL toluene was added 13.2 mL (180 mmol) thionyl chloride. The solution was heated at reflux under nitrogen for 3 hours. The excess thionyl chloride and toluene were distilled at atmospheric pressure under N2. The yellow residue was purified by kugelrohr distillation (bp=60°-65° C./0.1 mm Hg) and 13.8 g (64%) of the 2-bromooctanoyl chloride as a colorless oil was isolated.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. distillationThe excess thionyl chloride and toluene were distilled at atmospheric pressure under N2
  4. distillationThe yellow residue was purified by kugelrohr distillation (bp=60°-65° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-acd63c64178a4462a306cbb7bbee6c9f
Source dataset
uspto-grants-1995_05
Patent number
US05420305

Linked notes

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