Sodium borohydride → 4-Bromo-3-chloro-3,4,4-trifluorobutan-1-ol

Reaction equation

[Br:1][C:2]([F:10])([F:9])[C:3]([Cl:8])([F:7])[CH2:4][CH:5]=[O:6].[BH4-].[Na+]>>[Br:1][C:2]([F:10])([F:9])[C:3]([Cl:8])([F:7])[CH2:4][CH2:5][OH:6]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 218364804-Bromo-3-chloro-3,4,4-trifluorobutanal

Product 1

HCID 218364774-Bromo-3-chloro-3,4,4-trifluorobutan-1-ol

Procedure

Alternatively, the intermediate VII can be reduced with sodium borohydride without isolation to give 4-bromo-3-chloro-3,4,4-trifluorobutanol ((IX) in high yield; or by hydrolysis of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) to give IX. Oxidation of IX with Jones reagent to give VIII in 85% yield.

Sources & evidence

ORD record: ord-7b1c9b35e2d64ea98dcf2ea9f2964ba7
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05514717

Reaction notes

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