Hydrogen Peroxide → 4-Bromo-3,3,4,4-tetrafluorobutan-1-ol

HRID 2099004Notes

Reaction equation

HRID 2099004 reaction equation
[Br:1][C:2]([F:9])([F:8])[C:3]([F:7])([F:6])[CH:4]=[CH2:5].B.C12BC(CCC1)CCC2.[OH:20]O.[OH-].[Na+]>O1CCCC1.CCCCCC>[Br:1][C:2]([F:9])([F:8])[C:3]([F:7])([F:6])[CH2:4][CH2:5][OH:20]

Participants

8

Procedure

Also, the sulfonic acid salt of formula (1) can be synthesized by starting with 4-bromo-3,3,4,4-tetrafluoro-1-butene which is readily available in the industry, effecting hydroboration with a borane such as 9-borabicyclo[3.3.1]-nonane (9-BBN) in a solvent such as n-hexane or tetrahydrofuran by a standard technique, treating the product with an oxidizing agent such as aqueous hydrogen peroxide in the presence of a base such as sodium hydroxide to form 4-bromo-3,3,4,4-tetrafluorobutanol, and esterifying it with carboxylic halide in the presence of a base such as triethylamine.

Sources & evidence

ORD record
ord-59354e89896e48b684c260a3cbefcaa2
Source dataset
uspto-grants-2009_08
Patent number
US07569324B2

Reaction notes

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