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Bromine → 2-Bromo-4,4,4-trifluorobutyraldehyde

HRID 2361740
Notes
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Reaction equation

HRID 2361740 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][CH:5]=[O:6].[Br:9]Br>O1CCOCC1>[Br:9][CH:4]([CH2:3][C:2]([F:8])([F:7])[F:1])[CH:5]=[O:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24408BromineHCID 27770834,4,4-Trifluorobutanal

Product 1

HCID 580811402-Bromo-4,4,4-trifluorobutyraldehydeYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4,4,4-trifluorobutyraldehyde (5 g, 39.68 mmol) in 1,4-dioxane (5 ml) cooled to 0° C., bromine (2.24 ml, 43.65 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 2 h. The resulting reaction mixture was filtered through a pad of diatomaceous earth and the filtrate was washed with NaHCO3 (aqueous sat. solution). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield compound D4 (6.2 g, 76%) that was used in the next reaction step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered through a pad of diatomaceous earth
  3. washthe filtrate was washed with NaHCO3 (aqueous sat. solution)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-b900e6d946eb4e79b7397e274629fbd3
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691813B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes