2,6-Lutidine → (2E)-N-(3-Bromo-5-fluorophenyl)-3-phenylacrylamide

HRID 1644467Notes

Reaction equation

HRID 1644467 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].[C:10](Cl)(=[O:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C(C)=CC=CC=1C.BrC1C=C(NC(=O)/C=C/C2C=CC=CC=2)C=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

5

Reactant 4

HCID 79372,6-LutidineHCID 660233-Phenylprop-2-enoyl chlorideHCID 874919(2E)-N-(3-bromophenyl)-3-phenylprop-2-enamideHCID 150201553-Bromo-5-fluoroaniline2×

Product 1

HCID 66774736(2E)-N-(3-Bromo-5-fluorophenyl)-3-phenylacrylamideYield 85%

Procedure

The compound was prepared from 3-bromo-5-fluoroaniline (Intermediate 180, 5.3 g, 27.9 mmol) and cinnamoylchloride (5.6 g, 33.5 mmol) in the presence of 2,6-lutidine (5.0 mL, 41.9 mmol) as described for Intermediate 18 to give the product as a colorless solid, 7.6 g (85% yield).

Sources & evidence

ORD record
ord-db86264766014705b172ff686b8ef29e
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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