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. The resulting solution was then warmed to −20° C. and cooled again to −50° C. A solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture was allowed to warm to room temperature. The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2×150 mL). The combined organic phases were dried and concentrated. The product was recrystallized from hexane to give 3-bromo-6-chloro-2-fluorobenzaldehyde (40.0 g, 0.169 mol): mp 92-93° C.
Workup
- temperaturecooled again to −50° C
- temperatureto warm to room temperature
- customThe reaction was quenched with water (250 mL)
- extractionextracted with ethyl acetate (2×150 mL)
- customThe combined organic phases were dried
- concentrationconcentrated
- customThe product was recrystallized from hexane
Sources & evidence
- ORD record
- ord-93ec3e10bc7d4c07a244a560c29cf55c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199943B2
Reaction notes
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