Oxalyl chloride → 3-(4-Fluorophenyl)butyryl chloride

HRID 362858Notes

Reaction equation

HRID 362858 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14](C)[CH2:15]C(O)=O)=[CH:10][CH:9]=1>ClCCl>[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:15])[CH2:1][C:2]([Cl:4])=[O:3])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2919153-(4-fluorophenyl)butanoic acid

Product 1

HCID 232936303-(4-Fluorophenyl)butyryl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Oxalyl chloride (71 g, 48.8 ml, 0.560 mol, Aldrich) was added to a mixture of 3-(4-fluorophenyl)butyric acid (34 g, 0.187 mol) in 200 ml of dichloromethane at -5° C. After stirring for 20 min at this temperature, the solution was allowed to warm to 25° C. and stirring was continued for 2 h. The volatiles were removed by spin evaporation in vacuo with the addition of dichloromethane (4 ×) during concentration to give 35.1 g (94%) of 3-(4-fluorophenyl)butyryl chloride as a light yellow oil;

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe volatiles were removed by spin evaporation in vacuo with the addition of dichloromethane (4 ×) during concentration

Sources & evidence

ORD record
ord-4862d21e0d0649e3a1ea9ca986876ce7
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

Loading…