Dimethylformamide → m-Ethylbenzaldehyde

HRID 2105052Notes

Reaction equation

HRID 2105052 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH3:9])[CH:3]=1.C([Li])CCC.CN([CH:18]=[O:19])C>C1COCC1.C(OCC)C>[CH2:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:18]=[O:19])[CH3:9]

Participants

6

Reactant 3

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

Product 1

HCID 118623m-EthylbenzaldehydeYield 109.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-bromo-3-ethylbenzene (5 g, 27.2 mmol) in THF (135 mL) at −78° C. was added butyl lithium (1.6 M in hexanes, 18 mL, 28.8 mmol) dropwise. The mixture was stirred at −78° C. for 5 min. DMF (2.1 mL, 27.2 mmol) was added and the mixture was warmed to ambient temperature over 2 h. The mixture was diluted with diethyl ether (500 mL), washed with sat. NaHCO3 and brine, dried (Na2SO4) and concentrated to yield 4 g of Intermediate 370.1 as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (t, J=7.58 Hz, 3H) 2.73 (q, J=7.58 Hz, 2H) 7.39-7.51 (m, 2H) 7.64-7.76 (m, 2H) 9.99 (s, 1H).

Workup

  1. temperaturethe mixture was warmed to ambient temperature over 2 h
  2. washwashed with sat. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c22660b12b426bbc93be7cb8c64717
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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