Dimethylformamide → 4-Diethylamino-3-isopropylbenzaldehyde

HRID 1698421Notes

Reaction equation

HRID 1698421 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[C:15]([CH:24]([CH3:26])[CH3:25])[CH:14]=1.CN(C)[CH:29]=[O:30]>>[CH2:20]([N:19]([CH2:22][CH3:23])[C:16]1[CH:17]=[CH:18][C:13]([CH:29]=[O:30])=[CH:14][C:15]=1[CH:24]([CH3:26])[CH3:25])[CH3:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67276655(4-Bromo-2-isopropylphenyl)diethylamineHCID 178418244HCID 178418244, compound

Product 1

HCID 866465754-Diethylamino-3-isopropylbenzaldehydeYield 97.4%

Procedure

In a manner analogous to example 1 d, the process is carried out by a reaction of 1.8 ml (4.4 mmol) of 2.5M n-butyllithium/hexane with 1 g (3.7 mmol) of (4-bromo-2-isopropylphenyl)diethylamine and 0.35 ml (4.5 mmol) of dimethylformamide. 790 mg of 4-diethylamino-3-isopropylbenzaldehyde are obtained in the form of a yellow oil (yield=97%).

Workup

  1. customanalogous to example 1 d

Sources & evidence

ORD record
ord-218fd2203e5b4588b06b0fcdb172d684
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

Loading…