Hydrogen Bromide → 3-(3-Fluorophenyl)-7-hydroxychromen-4-one

HRID 1455030Notes

Reaction equation

HRID 1455030 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([O:19]C)=[CH:14][CH:15]=3)[O:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Br>O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=3)[O:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 179785443-(3-Fluorophenyl)-7-methoxychromen-4-one

Product 1

HCID 179785433-(3-Fluorophenyl)-7-hydroxychromen-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(3-Fluorophenyl)-7-methoxychromen-4-one (320 mg) was refluxed with 47% HBr (18 ml) until disappearance of the starting material. The mixture was poured into water and the precipitate was filtrated and dried yielding 3-(3-fluorophenyl)-7-hydroxychromen-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 10.87 (s, 1H), 8.49 (s, 1H), 7.99 (d, 1H, J 8.7 Hz), 7.43-7.49 (m, 3H), 7.20-7.24 (m, 1H), 6.97 (dd, 1H, J 8.7, 2.2 Hz), 6.90 (d, 1H, J 2.2 Hz).

Workup

  1. filtrationthe precipitate was filtrated
  2. customdried

Sources & evidence

ORD record
ord-6115607e79f5492b8fb44fe9a140481d
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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