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

HRID 1870266Notes

Reaction equation

HRID 1870266 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-b696efaa655a4de48f11d732af0c5ff8
Source dataset
uspto-grants-2000_08
Patent number
US06096781

Reaction notes

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