Water → Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoate

HRID 1168516Notes

Reaction equation

HRID 1168516 reaction equation
O.[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([I:10])=[CH:5][C:4]=1[C:11](=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:19]([O:21][CH:22](OCC)OCC)[CH3:20].C(OC(=O)C)(=O)C>C(O)C.C(OCC)(=O)C>[F:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([I:10])=[CH:5][C:4]=1[C:11]([C:12](=[CH:22][O:21][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 12083041Ethyl 3-(2,3-difluoro-5-iodophenyl)-3-oxopropanoate

Product 1

HCID 69879816Ethyl 2-(2,3-Difluoro-5-iodobenzoyl)-3-ethoxy-2-propenoateYield 98.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A flask equipped with a Dean-Stark trap and cold water condenser, is charged with ethyl 3-(2,3-difluoro-5-iodophenyl)-3-oxopropanoate (Preparation 20, 14.8 g), triethylorthoformate (12.4 g), and acetic anhydride (14.92 g). The contents are placed in an oil bath initially at 115° C. and the temperature quickly raised to 150° C. where it is maintained until the volume of ethyl acetate and ethanol distillate collected remained constant (ca. 1.25 h). The reaction mixture is cooled and concentrated at reduced pressure to obtain 16.86 g (98.5%) of the title compound as a dark golden oil. Physical characteristics: 1H NMR (CDCl3) δ8.98, 7.87-7.75, 7.71, 7.69-7.51, 4.36, 4.29-4.08, 3.75, 1.48, 1.35, 1.26, 1.21-1.02; MS (ESI+) m/z 411 (M+H)+.

Workup

  1. customThe contents are placed in an oil bath initially at 115° C.
  2. customcollected
  3. custom(ca. 1.25 h)
  4. temperatureThe reaction mixture is cooled
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-fe06ed0facec4eed93cda41113b0413c
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

Loading…