Methyl 2,4-dibromobutanoate → Diethyl 2-phenyl-3-cyano-6-chlorohexane-3,4-dicarboxylate

HRID 325769

Reaction equation

HRID 325769 reaction equation
[C:1]([CH:3]([CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Cl[CH:18]([CH2:24][CH2:25][Cl:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(C(C(C1C=CC=CC=1)C)C(OC)=O)#N.BrC(CCBr)C(OC)=O>>[C:11]1([CH:9]([C:3]([C:1]#[N:2])([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:24][CH2:25][Cl:26])[CH3:10])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 296716Methyl 2,4-dibromobutanoateHCID 11229687Ethyl 2-cyano-3-phenylbutyrateHCID 12613704Ethyl 2,4-dichlorobutanoateHCID 13276234Methyl 2-cyano-3-phenylbutyrate

Product 1

HCID 20279787Diethyl 2-phenyl-3-cyano-6-chlorohexane-3,4-dicarboxylate

Procedure

Ethyl 2-cyano-3-phenylbutyrate and ethyl 2,4-dichlorbutyrate can be used in place of methyl 2-cyano-3-phenylbutyrate and methyl 2,4-dibromobutyrate, respectively, in the alkylation reaction of Example 3 to produce the corresponding diethyl 2-phenyl-3-cyano-6-chlorohexane-3,4-dicarboxylate. The latter product can then be reacted with the tricarboxylate of Example 4 and the dicarboxylate of Example 7 to give the corresponding pentaester and tetraester products.

Workup

  1. customrespectively, in the alkylation reaction of Example 3

Sources & evidence

ORD record
ord-304a428e49ba483a847594332773dc38
Source dataset
uspto-grants-1984_04
Patent number
US04442298

Linked notes

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