Boron tribromide → 3-(4-Bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

HRID 632638Notes

Reaction equation

HRID 632638 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:9]=3[S:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 867306523-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

Product 1

HCID 867306533-(4-Bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-olYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 30 mL vial containing 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (100 mg, 0.23 mmol) in DCM (1 mL) was added BBr3 (1 M in hexanes, 0.680 mL, 0.68 mmol) and the reaction mixture was stirred for 1 h at room temperature. Upon completion the reaction was quenched with 4 mL MeOH and stirred for 10 min. The mixture was the concentrated in vacuo onto silica gel and the crude material was purified by column chromatography (SiO2, 1-100% EtOAc/Heptane) to afford 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (72 mg, 0.17 mmol, 77% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=7.47-7.57 (m, 2 H), 7.35-7.45 (m, 2 H), 7.20 (d, J=2.02 Hz, 1 H), 7.16 (d, J=8.59 Hz, 1 H), 6.73-6.90 (m, 5 H).

Workup

  1. customUpon completion the reaction was quenched with 4 mL MeOH
  2. stirringstirred for 10 min
  3. concentrationconcentrated in vacuo onto silica gel
  4. customthe crude material was purified by column chromatography (SiO2, 1-100% EtOAc/Heptane)

Sources & evidence

ORD record
ord-5507630c00464598a5940e1b24a4a3b5
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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