Ethyl cyanoacetate → HCID 11736980, compound

HRID 412832Notes

Reaction equation

HRID 412832 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([CH:14]([C:12]#[N:13])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

Product 1

HCID 11736980HCID 11736980, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Method A of the above general procedure was followed using 4-bromobenzotrifluoride (226 mg, 1.01 mmol), ethyl cyanoacetate (123 mg, 1.09 mmol), pentaphenylferrocenyl ligand (14 mg, 0.020 mmol) and Pd(dba)2 (6.0 mg, 0.010 mmol). The reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes) to give the desired product (213 mg, 82%) as a colorless oil: 1H NMR (CDCl3) δ 7.71-7.69 (m, 2H), 7.63-7.60 (m, 2H), 4.80 (s, 1H), 4.27 (dq, 7.2, 1.2 Hz, 2H), 1.30 (t, 7.2 Hz, 3H). 13C{1H} NMR (CDCl3) δ 164.28, 133.81, 131.66 (q, 33.0 Hz), 128.55, 126.38 (q, 3.7 Hz), 123.68 (q, 272.3 Hz), 115.00, 63.78, 43.52, 13.89.

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes)

Sources & evidence

ORD record
ord-77dfe2e14a8d4ab49b269134094dfab9
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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