Dimethylformamide → 3-Tert-butyl-5-chloro-4-dimethylaminobenzaldehyde

HRID 1698413Notes

Reaction equation

HRID 1698413 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N:20]([CH3:22])[CH3:21])=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=1.CN(C)[CH:29]=[O:30]>>[C:23]([C:15]1[CH:14]=[C:13]([CH:18]=[C:17]([Cl:19])[C:16]=1[N:20]([CH3:22])[CH3:21])[CH:29]=[O:30])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67276978(4-Bromo-2-tert-butyl-6-chlorophenyl)dimethylamineHCID 178418244HCID 178418244, compound

Product 1

HCID 866465713-Tert-butyl-5-chloro-4-dimethylaminobenzaldehydeYield 98.7%

Procedure

In a manner analogous to example 1 d, the process is carried out by a reaction of 2.25 ml (5.6 mmol) of 2.5M n-butyllithium/hexane with 1.5 g (5.2 mmol) of (4-bromo-2-tert-butyl-6-chlorophenyl)dimethylamine and 450 μl (5.8 mmol) of dimethylformamide. 1.23 g of 3-tert-butyl-5-chloro-4-dimethylaminobenzaldehyde are obtained in the form of a yellow oil (yield=99%).

Workup

  1. customanalogous to example 1 d

Sources & evidence

ORD record
ord-4b0c0a6cd09c4ca0b519ab201739e62d
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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