Oxalyl chloride → 4,4,4-Trifluorobutanoyl chloride

HRID 397958Notes

Reaction equation

HRID 397958 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5](O)=[O:6].C(Cl)(=O)C([Cl:13])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]([F:9])([F:8])[CH2:3][CH2:4][C:5]([Cl:13])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27770854,4,4-Trifluorobutanoic acid

Product 1

HCID 151044744,4,4-Trifluorobutanoyl chlorideYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Method 5 General Experimental: 4,4,4-Trifluorobutyric acid (70.0 mmol, 10.0 g) in CH2Cl2 (190 ml) was treated with oxalyl chloride (140 mmol, 12.3 ml) and DMF (1 drop), then heated to reflux for 1 h. Solvent and excess oxalyl chloride were removed from the volatile product by simple distillation of the reaction mixture at atmospheric pressure to provide crude 4,4,4-trifluorobutyric acid chloride (6.4 g). 1H NMR (CDCl3) δ3.20 (2H, t, J=7.2), 2.65-2.45 (2H, m).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. customSolvent and excess oxalyl chloride were removed from the volatile product by simple distillation of the reaction mixture at atmospheric pressure

Sources & evidence

ORD record
ord-3457df89a6ff4cc682b368a4d2df3080
Source dataset
uspto-grants-2003_08
Patent number
US06610730B2

Reaction notes

Loading…