Oxalyl chloride → HCID 15104473, compound

HRID 1741908Notes

Reaction equation

HRID 1741908 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3](O)=[O:4].C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl.CN(C)C=O>[CH3:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]([Cl:14])=[O:4]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27755364,4,4-Trifluoro-2-methylbutanoic acid

Product 1

HCID 15104473HCID 15104473, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-methyl-4,4,4-trifluorobutyric acid (172 g) in methylene chloride (150 mL) and N,N-dimethylformamide (3.5 mL) at 0° C., under nitrogen was added (dropwise) oxalyl chloride (125 mL). The mixture was allowed to warm to ambient temperature and stirred for 16 hours. After distillation of the solvent, distillation using a concentric tube distillation column (40 cm×15 mm) afforded 2-methyl-4,4,4-trifluorobutyryl chloride (about 99% purity, 79.87 g, 42%); bp 115.0°-116.0° C. (at atmospheric pressure, measured at room temperature as 763.27 mm Hg); GLC: tR =5.04 min; MS(CI): 139 (M+H-HCl).

Workup

  1. distillationAfter distillation of the solvent, distillation
  2. distillationdistillation column (40 cm×15 mm)

Sources & evidence

ORD record
ord-d206d4ce16cc4b8a804708e1a5b55863
Source dataset
uspto-grants-1994_08
Patent number
US05334765

Reaction notes

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