2-Fluoro-5-methoxybenzoic acid → 2-Fluoro-5-hydroxybenzoic acid

HRID 1418538Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([O:11]C)=[CH:4][CH:3]=1>Br>[F:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Fluoro-3-methoxybenzoic acid (500 mg, 2.94 mmol) was mixed with freshly distilled 48% HBr (20 mL) and heated at 100° C. for 14 h. Water and HBr were evaporated and the crude product (462 mg) was used without further purification. 1H NMR(CD3OD): δ 7.28-7.29 (m, 1H), 6.92-7.12 (m, 2 H); 13C NMR (CD3OD): δ 167.80, 157.26 (d, J=249 Hz), 154.77, 122.52 (d, J=10.4 Hz), 120.49 (d, J=11 Hz), 118.77 (d, J=19 Hz), 118.58.

Workup

customWater and HBr were evaporated
customthe crude product (462 mg) was used without further purification

Sources & evidence

ORD record: ord-fc5424d87609413fb6b469a9a2ff5158
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05883129

Reaction notes

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