Hydrochloric Acid → 6-Bromo-5,5,6,6-tetrafluorohexanoic acid

HRID 338821Notes

Reaction equation

HRID 338821 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:22])[CH:7]([CH2:13][CH2:14][C:15]([F:21])([F:20])[C:16]([Br:19])([F:18])[F:17])C(OCC)=O)C.Cl>>[Br:19][C:16]([F:17])([F:18])[C:15]([F:20])([F:21])[CH2:14][CH2:13][CH2:7][C:6]([OH:22])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 582609422-(4-Bromo-3,3,4,4-tetrafluorobutyl)-malonic acid diethyl ester

Product 1

HCID 582609356-Bromo-5,5,6,6-tetrafluorohexanoic acidYield 95%

Procedure

7000 g (26.4 mol) of 15% of sodium hydroxide aqueous solution was added to 1940 g (5.29 mol) of the objective 2-(4-bromo-3,3,4,4-tetrafluorobutyl)-malonic acid diethyl ester obtained as discussed above, followed by refluxing it for 2 hours. Upon cooling it to room temperature, 2900 g (29.1 mol) of concentrated hydrochloric acid (36%) is added in an iced bath, followed by extraction with diisopropyl ether. A residue obtained by distilling a solvent off was heated to 170° C. thereby obtaining 1338 g of the objective 6-bromo-5,5,6,6-tetrafluorohexanoic acid (95% yield) in the form of a brown liquid.

Workup

  1. customobtained
  2. temperatureby refluxing it for 2 hours
  3. extractionfollowed by extraction with diisopropyl ether
  4. customA residue obtained
  5. distillationby distilling a solvent
  6. temperatureoff was heated to 170° C.

Sources & evidence

ORD record
ord-f94c5b5881ab4ef0917297a7f93e8aca
Source dataset
uspto-grants-2014_11
Patent number
US08889888B2

Reaction notes

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