Bromine → 2-Bromo-4,4,4-trifluorobutyraldehyde
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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe resulting reaction mixture
- filtrationwas filtered through a pad of diatomaceous earth
- washthe filtrate was washed with NaHCO3 (aqueous sat. solution)
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-b900e6d946eb4e79b7397e274629fbd3
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691813B2
Reaction notes
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