Dimethylformamide → 3-Tert-butyl-4-dimethylaminobenzaldehyde

HRID 1698400Notes

Reaction equation

HRID 1698400 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:10])[CH3:9])=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.C([Li])CCC.CN([CH:23]=[O:24])C>>[C:11]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]([CH3:10])[CH3:9])[CH:23]=[O:24])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67276232HCID 67276232, compoundHCID 178418339Butyllithium

Product 1

HCID 866465663-Tert-butyl-4-dimethylaminobenzaldehydeYield 60.9%

Procedure

In a manner analogous to example 1 d, the process is carried out by a reaction of 4.1 g (16 mmol) of (4-bromo-2-tert-butylphenyl)dimethylamine with 9.6 ml (24 mmol) of a 2.5M solution of n-butyllithium and 1.9 ml (24 mmol) of DMF. 2 g of 3-tert-butyl-4-dimethylaminobenzaldehyde are obtained in the form of a yellow oil (yield=100%).

Workup

  1. customanalogous to example 1 d

Sources & evidence

ORD record
ord-6415bc0d5704446099a808e6ef7edb82
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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