Ethyl orthoformate → HCID 178500751, compound

HRID 2271522Notes

Reaction equation

HRID 2271522 reaction equation
[CH:1]1([C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.[CH:11](OCC)(OCC)OCC.[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][C:23]=1[F:29]>C(Cl)Cl>[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][CH:11]=[C:5]([C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:10])[C:6]([O:8][CH3:9])=[O:7])=[CH:24][C:23]=1[F:29]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 8218484-Bromo-3-fluoroanilineHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 178500751HCID 178500751, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A stirred mixture of methyl 3-cyclopropyl-3-oxopropanoate (3.49 g, 26.3 mmol), triethyl orthoformate (5.2 mL, 31.6 mmol), and 4-bromo-3-fluoroaniline (4.47 g, 26.0 mmol) was heated at 140° C. overnight with a Dean Stark trap. After this time the reaction was cooled to room temperature, diluted with methylene chloride and filtered through a pad of silica. The filtrate was concentrated to afford the desired product (7.5 g, 85%) as a light yellow solid: ESI MS m/z 343 [C14H13BrFNO3+H]+.

Workup

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. filtrationfiltered through a pad of silica
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-404bba82e9f145e2ba4879003fc45ceb
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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