4-Bromoaniline → HCID 178500750, compound

HRID 2271510Notes

Reaction equation

HRID 2271510 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][CH:23]=1>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][CH:23]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 31214Ethyl orthoformateHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 178500750HCID 178500750, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

A stirred mixture of methyl 3-cyclopropyl-3-oxopropanoate (20 g, 0.141 mol), triethyl orthoformate (28 mL, 0.169 mol), and 4-bromoaniline (24.2 g, 0.141 mol) were heated at 130° C. for 5 h 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 (26.5 g, 55%) as a yellow solid: ESI MS m/z 324 [C14H14BrNO2+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-140f38c1fde84ab99043527ca64ad70d
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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