4-Bromophenol → 3-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

HRID 632636Notes

Reaction equation

HRID 632636 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[C:13]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:14]=2[S:15](=[O:25])[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[C:13]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:14]=3[S:15](=[O:25])[C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 24758Sodium hydrideHCID 159594683-Bromo-6-methoxy-2-(4-methoxyphenyl)benzothiophene 1-oxide

Product 1

HCID 867306513-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromophenol (469 mg, 2.71 mmol) in DMF (3 mL) was added sodium hydride (60% suspension in oil, 108 mg, 2.71 mmol), the resulting mixture was allowed to stir for 10 min at room temperature. To the solution was added 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (900 mg, 2.46 mmol) as a solid. The reaction was heated to 80° C. for 18 h. Upon completing the reaction was cooled to room temperature, quenched with water and diluted with DCM. The organic phase was collected (phase separator) and concentrated in vacuo to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-60% EtOAc/Heptane) to afford 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (980 mg, 2.14 mmol, 87% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm==7.70-7.78 (m, 2 H), 7.53 (d, J=2.02 Hz, 1 H), 7.41 (d, J=8.59 Hz, 2 H), 6.90-7.06 (m, 6 H), 3.91 (s, 3 H), 3.83 (s, 3 H).

Workup

  1. temperatureThe reaction was heated to 80° C. for 18 h
  2. temperaturewas cooled to room temperature
  3. customquenched with water
  4. additiondiluted with DCM
  5. customThe organic phase was collected (phase separator)
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product
  8. customThe crude material was purified by column chromatography (SiO2, 0-60% EtOAc/Heptane)

Sources & evidence

ORD record
ord-56e1ce0c0d4a40d6a27062a06b424c40
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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