Trifluoroacetic anhydride → HCID 131728306, compound

HRID 505973Notes

Reaction equation

HRID 505973 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[C:20]([C:24]([C:27]([O:30][C:31]([C:37]([O:40][C:41]([CH2:47]O)([C:43]([F:46])([F:45])[F:44])[F:42])([F:39])[F:38])([C:33]([F:36])([F:35])[F:34])[F:32])([F:29])[F:28])([F:26])[F:25])([F:23])([F:22])[F:21]>O>[Br:14][CH2:15][CH2:16][C:17]([O:19][CH2:47][C:41]([O:40][C:37]([C:31]([O:30][C:27]([C:24]([C:20]([F:21])([F:22])[F:23])([F:25])[F:26])([F:28])[F:29])([C:33]([F:36])([F:35])[F:34])[F:32])([F:39])[F:38])([C:43]([F:46])([F:45])[F:44])[F:42])=[O:18]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 115533-Bromopropionic acidHCID 27361501H,1H-Perfluoro-2,5-dimethyl-3,6-dioxanonan-1-ol

Product 1

HCID 131728306HCID 131728306, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising trifluoroacetic anhydride (25.6 g) and 3-bromopropionic acid (17.9 g) was stirred at room temperature under a nitrogen stream for 1 hour. CF3CF2CF2OCF(CF3)CF2OCF(CF3)CH2OH (55.9 g) was added dropwise thereto while cooling with water so that the internal temperature would be maintained to be 30° C. or lower over a period of 30 minutes. 3 hours later, the reaction liquid was directly concentrated and purified by silica gel column chromatography (eluent: mixed solvent comprising hexane (10): ethyl acetate (1)) to obtain the title compound (54.6 g). The yield: 80%.

Workup

  1. temperaturewould be maintained
  2. custom3 hours later, the reaction liquid
  3. concentrationwas directly concentrated
  4. custompurified by silica gel column chromatography (eluent: mixed solvent comprising hexane (10): ethyl acetate (1))

Sources & evidence

ORD record
ord-9252048dea0348d5a25995244bce3343
Source dataset
uspto-grants-2010_08
Patent number
US07781612B2

Reaction notes

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