Methanol → 2-(4-Methoxyphenyl)-1-benzothiophene-6-ol

HRID 1870270Notes

Reaction equation

HRID 1870270 reaction equation
[CH3:1][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(C)C)[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.CO>C(Cl)Cl>[CH3:1][O: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

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 9882733HCID 9882733, compound

Product 1

HCID 98379882-(4-Methoxyphenyl)-1-benzothiophene-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

2-(4-Methoxyphenyl)-6-isopropoxybenzo[b]thiophene (1.0 g, 3.35 mmol) was dissolved in 10 mL of methylene chloride and warmed to 30° C. Boron trichloride (3.685 35 mL, 3.685 mmol 1M in methylene chloride) was slowly added to the stirring reaction solution. The reaction was allowed to proceed for one hour at ambient temperature. The reaction was quenched with the dropwise addition of methanol (0.536 g, 16.75 mmol). The reaction was stirred for two hours and a white precipitate formed. The solid as filtered off, washed three times with 10 mL portions of methylene chloride and dried to yield the title compound as a white solid. EA calculated for C15H12O2S: C, 70.29; H, 4.72; S, 12.51. Found: C, 67.69; H, 4.65; S, 12.02. MS(FD): m/e=256 (M+).

Workup

  1. customa white precipitate formed
  2. filtrationThe solid as filtered off
  3. washwashed three times with 10 mL portions of methylene chloride
  4. customdried

Sources & evidence

ORD record
ord-dfda4644d8bc4910aa227c3480f618e8
Source dataset
uspto-grants-2000_08
Patent number
US06096781

Reaction notes

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