Water → 1-Fluoro-4-[2-(4-nitrophenyl)ethenyl]benzene

HRID 1827427Notes

Reaction equation

[H-].[Na+].C(OP([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)(=O)OCC)C.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.O>CN(C)C=O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.63 g of sodium hydride are added to 50 ml of dimethylformamide. The mixture is cooled to 0° C. and 16 g (58.6 mmol) of (4-nitro-benzyl)-phosphonic acid diethyl ester is added portionwise. The solution is stirred at room temperature for 1.5 h, then cooled to −10°. A solution of 6.09 g (50 mmol)4-fluoro-benzaldehyde in 10 ml dimethylformamide is slowly added to the mixture at −10°. Stirring at room temperature for 45 min followed by additon of 250 ml water yields a precipitate which is filtered and recrystallised from ethanol/water 85:15 to yield 10.81 g (91%) of a yellow solid. MS: m/e=243.1 (M+).

Workup

temperaturecooled to −10°
stirringStirring at room temperature for 45 min
customyields a precipitate which
filtrationis filtered
customrecrystallised from ethanol/water 85:15

Sources & evidence

ORD record: ord-480de259b5c743eba2bf360583de6519
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053245B2

Reaction notes

Loading…