3-Fluoroaniline → HCID 59401185, compound

HRID 1255005Notes

Reaction equation

HRID 1255005 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19]>>[F:14][C:10]1[CH:9]=[C:8]([CH:2]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:16]([F:15])[CH:17]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 20711243Ethyl 2-bromo-2-(3-fluorophenyl)acetate

Product 1

HCID 59401185HCID 59401185, compoundYield 99%

Procedure

A solution of ethyl 2-bromo-2-(3-fluorophenyl)acetate (I9) (1.80 g, 6.84 mmol) in 3-fluoroaniline (6.50 mL, 68.0 mmol) is heated at 100° C. for 5 minutes under MW irradiation (LC-MS monitoring: complete conversion). The solvent is evaporated and the resulting crude is purified by flash chromatography (Hexane/EtOAc=9/1) in order to obtain 2.00 g of I10 as a yellow oil (99% yield).

Workup

  1. customThe solvent is evaporated
  2. customthe resulting crude is purified by flash chromatography (Hexane/EtOAc=9/1) in order

Sources & evidence

ORD record
ord-5a3c0167b09242168f8326670cd5b26e
Source dataset
uspto-grants-2013_06
Patent number
US08455646B2

Reaction notes

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