6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene → 2-(4-Hydroxyphenyl)benzo(b)thiophen-6-ol

HRID 1937643Notes

Reaction equation

HRID 1937643 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1>Br.C(O)(=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

Product 1

HCID 4459202-(4-Hydroxyphenyl)benzo(b)thiophen-6-olYield 75.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

2-(4-Methoxyphenyl)-6-methoxybenzo[b]thiophene (10 g, 35.5 mmol) was suspended in 50 mL of 48% aqueous hydrobromic acid and 100 mL of glacial acetic acid. The reaction was heated to reflux under a nitrogen atmosphere for 120 hours. The reaction was allowed to cool and filtered. The solid product was washed with water and dried to yield 6.46 g of the title compound. 1H NMR: (CDCl3-d6DMSO): δ 7.54 (d, 1H), 7.48 (d, 2H), 7.27 (s, 1H), 7.24 (m, 1H), 6.92 (d, 1H), 6.85 (d, 2H). MS(FD): m/e=242 (M+).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux under a nitrogen atmosphere for 120 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. washThe solid product was washed with water
  6. customdried

Sources & evidence

ORD record
ord-7392f487993445feb5f4f658f61f6b2b
Source dataset
uspto-grants-2002_05
Patent number
US06395769B1

Reaction notes

Loading…