Thionyl Chloride → HCID 14391759, compound

HRID 1651473Notes

Reaction equation

HRID 1651473 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH2:11][CH3:12])[C:8](O)=[O:9])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].S(Cl)([Cl:21])=O>C(Cl)Cl.N1C=CC=CC=1>[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH2:11][CH3:12])[C:8]([Cl:21])=[O:9])=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 143917602-[4-Fluoro-3-(trifluoromethyl)phenoxy]butanoic acid

Product 1

HCID 14391759HCID 14391759, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To 1.2 g (4.5 mmole) of (-)-2-(4-fluoro-3-trifluoromethylphenoxy)butanoic acid dissolved in 15 ml methylene chloride was added one drop of pyridine and further added dropwise 0.6 g of thionyl chloride. The reaction mixture was further stirred at room temperature for 4 hours and then thionyl chloride and methylene chloride were removed under reduced pressure to obtain 1.2 g of (-)-2-(4-fluoro3-trifluoromethylphenoxy)butanoic acid chloride. The resulting mixture was applied for the next reaction without purification.

Workup

  1. customthionyl chloride and methylene chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-eb7094016a674902ad35a15405ba2e5a
Source dataset
uspto-grants-1990_05
Patent number
US04929273

Reaction notes

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