4-(4-Fluorobenzoyl)isophthalic acid → 1-(4-Fluorophenyl)-1,3-dihydro-3-oxo-5-isobenzofurancarboxylic acid

HRID 432048Notes

Reaction equation

[C:1]([C:4]1[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:7])(O)=[O:2]>C(O)(=O)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([CH:6]2[C:5]3[C:4](=[CH:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][CH:15]=3)[C:1](=[O:2])[O:7]2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Zink (38 g, 0.58 mol) was suspended in acetic acid (400 mL). The mixture was heated to 60° C. 2,4-dicarboxy-4′-fluoro-benzophenone (21 g, 0.075 mol) was added in portions of 5 grams. After addition, the reaction mixture was heated at reflux temperature for two hours. The suspension was filtered while it was still hot. The filtrate was added to ice-water (1 kg) and the title compound was isolated by filtration. Yield 17.8 g (90%). 1H NMR (d6-DMSO): δ 6.84 (s, 1H), 7.17 (t, 2H), 7.43 (dd, 2H), 7.59 (d, 1H), 8.31 (d, 1H), 8.35 (s, 1H).

Workup

additionAfter addition
temperaturethe reaction mixture was heated
temperatureat reflux temperature for two hours
filtrationThe suspension was filtered while it
additionThe filtrate was added to ice-water (1 kg)

Sources & evidence

ORD record: ord-4fa0896e7a164ae0b322dd2dc8b99e6a
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660873B2

Reaction notes

Loading…