Hydrochloric Acid → 2-(4-Hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

HRID 1794499Notes

Reaction equation

HRID 1794499 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.C[O-].[Na+].Cl.C[CH2:24][O:25]C(C)=O>CN(C=O)C>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[O:9][C:10]3[C:2]([O:25][CH3:24])=[CH:3][C:4]([OH:18])=[CH:5][C:6]=3[CH:7]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 102863527-Bromo-2-(4-hydroxy-phenyl)-benzofuran-5-olHCID 10942334Sodium Methoxide

Product 1

HCID 102860222-(4-Hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A solution consisting of 58 (1.5 g, 4.9 mmol) in DMF (25 mL) was treated with CulBr (1.0 g, 6.5 mmol) and NaOMe (6 mL, 4.4 N in MeOH, 27 mmol) and heated to 160° C. for approximately 1 hour. The reaction mixture was allowed to cool and then worked up by adding 2 N HCl and EtOAc. The EtOAc layer was washed with NaHCO3 aq, brine and dried over MgSO4. The solution was concentrated and chromatographed on silica gel (1:4 EtOAc/hexanes to 3:7 EtOAc/hexanes) to yield 0.47 g of pdt: Mp=167–168° C., 1H NMR (DMSO-d6) δ 9.84 (br s, 1 H), 9.18 (br s, 1 H), 7.67 (d, 2 H, J=8.6 Hz), 6.99 (s, 1 H), 6.86 (d, 2 H, J=8.7 Hz), 6.46 (d, 1 H, J=2.1 Hz), 6.34 (d, 1 H, J=2.1 Hz), 3,89 (s, 3 H); MS 257 (M+H)+.

Workup

  1. temperatureto cool
  2. washThe EtOAc layer was washed with NaHCO3 aq, brine
  3. dry with materialdried over MgSO4
  4. concentrationThe solution was concentrated
  5. customchromatographed on silica gel (1:4 EtOAc/hexanes to 3:7 EtOAc/hexanes)
  6. customto yield 0.47 g of pdt

Sources & evidence

ORD record
ord-a68200eddbdb4e69abf935000b0bb0e3
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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