Acetic Acid → Diisopropylether ethyl acetate

HRID 433580Notes

Reaction equation

HRID 433580 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Cl:10])[NH2:6].[CH:13]([O:20][CH2:21][CH3:22])(OCC)OCC.[N+:23]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([O-])=O.[C:32]([OH:35])(=O)[CH3:33]>[Fe]>[Cl:10][C:9]1[CH:8]=[CH:7][C:5]([N:6]2[CH:32]=[C:22]([CH2:21][OH:20])[N:23]=[CH:26]2)=[CH:4][C:3]=1[C:2]([F:1])([F:11])[F:12].[CH3:31][CH2:30][O:29][C:27]([CH3:26])=[O:28].[O:35]([CH:8]([CH3:7])[CH3:9])[CH:32]([CH3:33])[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 69379Ethyl nitroacetate

Product 2

HCID 22281796Diisopropylether ethyl acetateHCID 23444982HCID 23444982, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

3-Trifluoromethyl-4-chloroaniline was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced with BH3 THF complex followed by hydrolytic workup and the title compound, Mp. 148-153° C. (AcOEt/iPr2O), MS: m/e=276 (M+), was obtained as a white crystalline solid.

Sources & evidence

ORD record
ord-72c65ce3307745448a9ccd49e2c474c4
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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