4-Bromoaniline → HCID 178450480, compound

HRID 2271528Notes

Reaction equation

HRID 2271528 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:12](OCC)(OCC)OCC.[Br:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>>[Br:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][CH:12]=[C:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 31214Ethyl orthoformateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 178450480HCID 178450480, compoundYield 32%

Conditions

Temperature
120 °C

Procedure

A stirred mixture of ethyl 3-oxohexanoate (12.1 mL, 75 mmol), triethyl orthoformate (16.6 mL, 100 mmol), and 4-bromoaniline (12.9 g, 75 mmol) were heated at 120° C. for 4 h with a Dean Stark trap. After this time the reaction was cooled to room temperature. The resultant solid was triturated with diethyl ether to afford the desired product (8.17 g, 32%) as a white solid. ESI MS m/z 340 [C15H18BrNO3+H]+

Workup

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-6f75e90dcfd84b92826dfc589e0453ff
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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