Water → 7-Methoxybenzo[b]thiophene

HRID 1986202Notes

Reaction equation

HRID 1986202 reaction equation
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:11][O-:12].[Na+].O>CN(C=O)C.[Cu](I)I>[CH3:11][O:12][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 120455387-Bromobenzo[b]thiophene

Product 1

HCID 110842177-Methoxybenzo[b]thiopheneYield 98.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-bromobenzo[b]thiophene (10.0 g, 46.9 mmol) in dry DMF (234 mL) is added copper iodide (8.90 g, 46.9 mmol), followed by the addition of sodium methoxide (30% in MeOH, 176 mL, 938 mmol) at room temperature under nitrogen atmosphere. The mixture is heated at 100° C. for 2 hours and cooled to room temperature. Water (400 mL) is added and the mixture is extracted with diethyl ether (4×200 mL). Organic layers are washed with cooled water (3×75 mL), saturated aqueous sodium chloride (100 mL), dried (MgSO4), and concentrated to give the title compound as yellow oil (7.58 g, 98% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture is extracted with diethyl ether (4×200 mL)
  3. washOrganic layers are washed with cooled water (3×75 mL), saturated aqueous sodium chloride (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dbffcf736d904a3989985425ab6f2498
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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