Dimethylformamide → m-Ethylbenzaldehyde
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH3:9])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CN(C)[CH:17]=[O:18]>O1CCCC1>[CH2:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:17]=[O:18])[CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-bromo-ethylbenzene (25 g) in dry tetrahydrofuran (350 ml) at −70° C. was treated dropwise with n-butyllithium (59 ml of a 2.5M solution in hexanes) and stirred for 1 hour. N,N-Dimethylformamide (30 ml) was added and the solution was stirred at −70° C. for 1 hour and allowed to warm to room temperature. The reaction mixture was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic phase was washed with 1N hydrochloric acid, dried (MgSO4) and evaporated.
Workup
- stirringthe solution was stirred at −70° C. for 1 hour
- customThe reaction mixture was partitioned between saturated ammonium chloride solution and ethyl acetate
- washThe organic phase was washed with 1N hydrochloric acid
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-0133cb16fb0d4941a628eec4a0bbb843
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218376B1
Reaction notes
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