Acetic Anhydride → 2-(2-Fluorophenyl)-3-(4-methylthiophenyl)propenoic acid

HRID 1378594Notes

Reaction equation

C(OC(=O)C)(=O)C.[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([OH:28])=[O:27].C(N(CC)CC)C>O>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=[CH:14][C:13]1[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=1)[C:26]([OH:28])=[O:27]

Participants

Conditions

Temperature: 90 °C

Procedure

Acetic anhydride (60 mL), 4-(methylthio)benzaldehyde (7.05 g, 44 mmol), 2-fluorophenylacetic acid (7.79 g, 50.5 mmol), and triethylamine (5.50 g, 54.5 mmol) were placed in a 250 mL round bottom flask and heated to reflux for 1.75 hours. The reaction was cooled to 90° C., and water (100 mL) was added cautiously through an addition funnel. This caused the solution to reflux vigorously and the temperature to rise to 135° C. A yellow precipitate formed and after cooling to room temperature the solid was collected by filtration, washed with water, and recrystallized from toluene to provide 2-(2-fluorophenyl)-3-(4-methylthiophenyl)propenoic acid as yellow needles (7.98 g, 63%): mp 151.5°-156.0° C. 1H NMR (CDCl3) 300 MHz 8.01 (s,1H), 7.41-7.00 (m, 8H), 2.43 (s, 3H). 19F NMR (CDCl3) -113.40 (m). Mass spectrum M+H+ =289.

Workup

temperatureheated
temperatureto reflux for 1.75 hours
temperatureto reflux vigorously
customto rise to 135° C
customA yellow precipitate formed
temperatureafter cooling to room temperature the solid
filtrationwas collected by filtration
washwashed with water
customrecrystallized from toluene

Sources & evidence

ORD record: ord-266ed69d3dc04df48cc4e603f44788a7
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05668161

Reaction notes

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