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

HRID 332867Notes

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

Participants

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

extractionextracted with DCM
customThe organic layer was collected (phase separator)
concentrationconcentrated in vacuo
customto afford the crude product which
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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