Phosphorus tribromide → 4-Bromo-1,1,1,2,2-pentafluorobutane

HRID 1801408Notes

Reaction equation

[Br:1][CH:2]=[CH:3][C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].P(Br)(Br)Br.FC(F)(C(F)(F)F)CCO>>[Br:1][CH2:2][CH2:3][C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6]

Participants

Reactant 3

HCID 24614Phosphorus tribromide

HCID 1086443,3,4,4,4-Pentafluorobutan-1-ol

HCID 534350621-Bromo-3,3,4,4,4-pentafluoro-1-butene

Product 1

HCID 125713504-Bromo-1,1,1,2,2-pentafluorobutane

Procedure

1-Bromo-3,3,4,4,4-pentafluoro-1-butene may be prepared by a three-step sequence beginning with reaction of phosphorous tribromide with 3,3,4,4,4-pentafluoro-1-butanol to give 4-bromo-1,1,1,2,2-pentafluorobutane. Thermal bromination of 4-bromo-1,1,1,2,2-pentafluorobutane at 350-400° C. gives 4,4-dibromo-1,1,1,2,2-pentafluorobutane, which may in turn be heated with powdered potassium hydroxide to give the desired bromobutene.

Sources & evidence

ORD record: ord-66ee78fbfc6944b8880354238b424e4e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349213B2

Reaction notes

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