Acetic Acid → Diisopropylether ethyl acetate

HRID 1841211Notes

Reaction equation

HRID 1841211 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-f7b0e349c4b549b6aa22d60a94c603f5
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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