Nitromethane → (E)-1-Chloro-4-(4-(2-nitrovinyl)phenoxy)-2-(trifluoromethyl)benzene

HRID 920290Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].C([O-])(=O)C.[NH4+].[N+:26]([CH3:29])([O-:28])=[O:27]>CC(O)=O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10](/[CH:11]=[CH:29]/[N+:26]([O-:28])=[O:27])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-(4-Chloro-3-(trifluoromethyl)phenoxy)benzaldehyde (13 g, 43.2 mmol) and ammonium acetate (1.67 g, 21.62 mmol) in HOAc (40 mL), was added nitromethane (6.99 mL, 130 mmol). The reaction mixture was stirred at 120° C. for 5 h, and concentrated. The residue was dissolved in DCM (150 mL), washed with sat. aqueous NaHCO3 (100 mL×2), brine and then, dried over anhydrous Na2SO4 and concentrated to afford the title compound as a brown solid (14.3 g, 63% yield).

Workup

concentrationconcentrated
dissolutionThe residue was dissolved in DCM (150 mL)
washwashed with sat. aqueous NaHCO3 (100 mL×2), brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-b097404ac136458f9bc43d512de4ac33
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273054B2

Reaction notes

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