5-Bromo-2-(2-fluoro-4-methoxyphenoxy)benzoic acid → 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one

HRID 335914Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[F:20])=[C:6]([CH:10]=1)[C:7]([OH:9])=O>O>[Br:1][C:2]1[CH:10]=[C:6]2[C:5]([O:11][C:12]3[C:13]([F:20])=[CH:14][C:15]([O:18][CH3:19])=[CH:16][C:17]=3[C:7]2=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

5-bromo-2-(2-fluoro-4-methoxyphenoxy)benzoic acid (28.5 g, 84 mmol) and polyphosphoric acid (205 g, 2089 mmol) were combined and heated at 125° C. for two hours. The solution was diluted with water (1 L) and filtered. The solids were washed well with 2N NaOH, then with water. The solids were then dried under vacuum to afford 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one as an off white solid. MS m/z=323.0 [M+H].

Workup

filtrationfiltered
washThe solids were washed well with 2N NaOH
customThe solids were then dried under vacuum

Sources & evidence

ORD record: ord-1239cf11a1294abeafd18d2c65bd3ea7
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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