Dimethylformamide → 3-Bromo-6-chloro-2-fluorobenzaldehyde
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[F:9].[Li+].CC([N-]C(C)C)C.CN([CH:21]=[O:22])C>C1COCC1>[Br:1][C:2]1[C:3]([F:9])=[C:4]([C:5]([Cl:8])=[CH:6][CH:7]=1)[CH:21]=[O:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. and a solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture was warmed to ambient temperature. The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2×150 mL) and the combined organic phases were dried (sodium sulfate) and concentrated. The solid residue was recrystallized from hexane to give 3-bromo-6-chloro-2-fluorobenzaldehyde (40.0 g, 0.169 mol): mp 92-93° C.
Workup
- additionAfter addition the solution
- temperaturecooled to −50° C.
- temperaturethe reaction mixture was warmed to ambient temperature
- customThe reaction was quenched with water (250 mL)
- extractionextracted with ethyl acetate (2×150 mL)
- dry with materialthe combined organic phases were dried (sodium sulfate)
- concentrationconcentrated
- customThe solid residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-9e560e11d2cb4d4284c5573b886e0e13
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07498468B2
Reaction notes
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