Sevoflurane → HCID 11310679, compound

HRID 1667575Notes

Reaction equation

[CH2:1](F)[O:2][CH:3]([C:8]([F:11])([F:10])[F:9])[C:4]([F:7])([F:6])[F:5].FC(F)(F)C(O)C(F)(F)F.BrC[C:25]([O:27]CC)=[O:26]>>[F:5][C:4]([F:7])([F:6])[CH:3]([O:2][CH2:1][C:25]([OH:27])=[O:26])[C:8]([F:11])([F:10])[F:9]

Participants

Reactant 3

HCID 5206Sevoflurane

HCID 7748Ethyl bromoacetate

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanol

Product 1

HCID 11310679HCID 11310679, compoundYield 66%

Procedure

U.S. Pat. No. 6,271,422 describes the synthesis of sevoflurane by fluoromethylation of alcohols via decarboxylative halogenation. In this way, hexafluoroisopropanol is submitted to reaction with ethyl alpha-bromoacetate providing alpha-(hexafluoroisopropoxy) acetic acid in a yield of 66%. This intermediate is subjected to reaction with the highly toxic lead tetra-acetate, using the carcinogenic benzene as the solvent. In the reaction sequence, the homogeneous benzene/sevochlorane solution, which is inseparable by distillation, is reacted with potassium fluoride providing at the end of the process sevoflurane with a low yield of 28%.

Sources & evidence

ORD record: ord-98b795fe4a1b4475b4ddd3a95e5e2932
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044247B2

Reaction notes

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