1-Bromo-2-Chloroethane → Ethyl 2-[(2-chloroethoxy)imino]-3-oxobutanoate

HRID 435276Notes

Reaction equation

HRID 435276 reaction equation
[OH:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:15][CH2:14][CH2:13][O:1][N:2]=[C:3]([C:9](=[O:11])[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178472877HCID 178472877, compound

Product 1

HCID 54193086Ethyl 2-[(2-chloroethoxy)imino]-3-oxobutanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-hydroxyimino-3-oxobutyrate (syn isomer, 60 g.), 1-bromo-2-chloroethane (54.1 g.), potassium carbonate (78 g.) and N,N-dimethylformamide (200 ml.) were treated in a similar manner to that of Example F-(1) to give ethyl 2-(2-chloroethoxyimino)-3-oxobutyrate (syn isomer, 83.6 g.), oil.

Sources & evidence

ORD record
ord-0ecf4661e10a4ee5aadee9f0332951aa
Source dataset
uspto-grants-1983_08
Patent number
US04400379

Reaction notes

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