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Sodium Bisulfate → 3-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

HRID 332867
Notes
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Reaction equation

HRID 332867 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[C:8]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:9]=3[S:10](=O)[C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[C:8]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:9]=3[S:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 21226445Aluminium lithium hydrideHCID 867306513-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

Product 1

HCID 867306523-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneYield 91%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (970 mg, 2.12 mmol) in THF (5 mL) was cooled to 0° C. To the cooled solution was added LAH (129 mg, 3.39 mmol) in one portion. The reaction mixture was stirred at 0° C. for 30 min after which the mixture was poured into 1 M aq. NaHSO4 solution and extracted with DCM. The organic layer was collected (phase separator) and concentrated in vacuo to afford the crude product which was purified by column chromatography (SiO2, 0-30% EtOAc/Heptane) to afford 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (850 mg, 1.93 mmol, 91% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm=3.83 (s, 3H), 3.90 (s, 3H), 6.80-6.99 (m, 5H), 7.22-7.32 (m, 2H), 7.32-7.44 (m, 2H), 7.65 (d, J=9.09 Hz, 2H).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was collected (phase separator)
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product which
  5. customwas purified by column chromatography (SiO2, 0-30% EtOAc/Heptane)

Sources & evidence

ORD record
ord-d8625f1427ee49018664f2e9d7c7a01e
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877801B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes