1-Bromo-3-chloropropane → 5-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

HRID 65301

Reaction equation

HRID 65301 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH:14]([CH3:16])[CH3:15])([CH2:20][CH2:21][CH2:22][Cl:23])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24533Sodium amideHCID 893962-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

Product 1

HCID 6199535-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Alternatively, one may prepare compounds of the invention via the procedures of Scheme III. In the first step, a derivative of formula 6a (see Scheme II) is alkylated with a 1,3-dihalopropane using a strong base in a suitable aprotic solvent to produce a derivative of formula 21 (step 1). For example, 2-(3,4-dimethoxyphenyl)-2-isopropylacetonitrile is treated with sodium amide in toluene and 1-bromo-3-chloropropane to produce 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-chloropropyl)-acetonitrile (21).

Sources & evidence

ORD record
ord-48303057aabd4f9c89aab8dcf056d73b
Source dataset
uspto-grants-1986_09
Patent number
US04613606

Linked notes

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