Benzeneacetonitrile, 4-fluoro- → (Z)-2-(4-fluorophenyl)-3-(5-methyl-2-nitrophenyl)acrylonitrile

HRID 717757Notes

Reaction equation

[Na].C[O-].[Na+].[F:5][C:6]1[CH:14]=[CH:13][C:9]([CH2:10][C:11]#[N:12])=[CH:8][CH:7]=1.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([N+:24]([O-:26])=[O:25])=[C:20]([CH:23]=1)[CH:21]=O>CO>[F:5][C:6]1[CH:14]=[CH:13][C:9](/[C:10](=[CH:21]/[C:20]2[CH:23]=[C:16]([CH3:15])[CH:17]=[CH:18][C:19]=2[N+:24]([O-:26])=[O:25])/[C:11]#[N:12])=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium metal (0.836 g, 0.0363 mol) was dissolved in MeOH (40 mL), and the resulting sodium methoxide solution was cooled to 0° C. To this was added 4-fluorobenzyl cyanide (4.9 g, 0.0363 mol), and the mixture stirred for 30 min. at 0° C. 5-Methyl-2-nitrobenzaldehyde (3.0 g, 0.0181 mol) was added at the same temperature, and the reaction mixture was stirred for a further 1 h at 0° C. After completion of reaction (monitored by TLC), the precipitated solid was isolated by filtration to give the desired compound as a light yellow colored solid (3.0 g, 58% yield).

Workup

stirringthe reaction mixture was stirred for a further 1 h at 0° C
customAfter completion of reaction (monitored by TLC)
customthe precipitated solid was isolated by filtration

Sources & evidence

ORD record: ord-3bd179db1e49479588f62d53ab02be8e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193728B2

Reaction notes

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