Ethyl trifluoroacetate → 1-[3-[2-(Dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanone

HRID 1383927Notes

Reaction equation

HRID 1383927 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1)[CH3:3].[F:14][C:15]([F:22])([F:21])[C:16](OCC)=[O:17].CN(CCOC1C=CC(C(=O)C(F)(F)F)=CC=1)C>>[CH3:1][N:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:16](=[O:17])[C:15]([F:22])([F:21])[F:14])[CH:10]=[CH:11][CH:12]=1)[CH3:3]

Participants

4

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 413371[2-(3-Bromophenoxy)ethyl]dimethylamineHCID 18319033HCID 18319033, compound

Product 1

HCID 183191361-[3-[2-(Dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanoneYield 44%

Procedure

N,N-Dimethyl-2-(3-bromophenoxy)ethylamine (2.87 g, 11.7 mmol) and ethyl trifluoroacetate (2.5 g, 17.6 mmol) were reacted by the general procedure as described in the preparation of [4-[2-(N,N-dimethylamino)ethoxy]phenyl]-2,2,2-trifluoroethanone. The residue was distilled under reduced pressure to afford the title compound (1.34 g, 44%) as a pale yellow liquid. Analytically pure sample was obtained by a second distillation under reduced pressure. Analysis for C12H14F3NO2.0.8H2O calcd. C 52.29%, H 5.70%, N 5.08%; Found: C 52.61%, H 5.53%, N 4.96%.

Workup

  1. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-09a267b45dfc47bbb1231692c12b2edc
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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