Boron tribromide → HCID 59611582, compound

HRID 72055Notes

Reaction equation

HRID 72055 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([O:17]C)[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]3[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 167197572-(4-Bromophenyl)-6-methoxybenzo[b]thiophene

Product 1

HCID 59611582HCID 59611582, compoundYield 88%

Procedure

To a stirred solution of 2-(4-bromo-phenyl)-6-methoxy-benzo[b]thiophene (80 mg, 0.25 mmol) was added BBr3 (0.5 mL of 1 M in DCM, 0.5 mmol) at 0° C. The mixture was stirred for 3 hours at ambient temperature. DCM was removed under vacuum, and the residue was dissolved in ethyl acetate (30 mL). The organic layer was washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was treated with hexane to give the product (67 mg, 88%). m/z 303.0, 305.0 (M−H)−.

Workup

  1. customDCM was removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. washThe organic layer was washed with NaHCO3 solution, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionThe obtained residue was treated with hexane

Sources & evidence

ORD record
ord-163ffb7babc54b949918ee4125254491
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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