Dimethylformamide → m-Ethylbenzaldehyde

HRID 324399

Reaction equation

HRID 324399 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

HCID 6228DimethylformamideHCID 123170Benzene, 1-bromo-3-ethyl-HCID 178418339Butyllithium

Product 1

HCID 118623m-Ethylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. stirringthe solution was stirred at −70° C. for 1 hour
  2. customThe reaction mixture was partitioned between saturated ammonium chloride solution and ethyl acetate
  3. washThe organic phase was washed with 1N hydrochloric acid
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-0133cb16fb0d4941a628eec4a0bbb843
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

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