Boron tribromide → [2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][3-methylphenyl]methanone

HRID 1956807Notes

Reaction equation

HRID 1956807 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)=[O:21])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)=[O:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 17760556[2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][3-methylphenyl]methanone

Product 1

HCID 17760557[2-(4-Hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl][3-methylphenyl]methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

1 g (3 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][3-methylphenyl]methanone was dissolved in 29 mL of CH2Cl2 and cooled to -70° C. To the stirring solution was added 20 mL of 1M BBr3 in CH2Cl2 in small portions over a ten minute period. The reaction was allowed to proceed under a nitrogen atmosphere, slowly warming to ambient temperature. After sixteen hours, the reaction was quenched by adding 1N NaOH and extracted with 200 mL of EtOAc. The EtOAc layer was separated and washed with water, dried by filtration through anhydrous Na2 SO4, and evaporation to dryness, in vaccuo. The crude product was purified by chromatography on a silica gel column eluted with EtOAc-hexane (1:4)(v/v). The product was rechromatographed on a silica gel column eluted with EtOAc-hexane (1:3)(v/v). This yielded 190 mg of the title compound as a yellow amorphous powder.

Workup

  1. temperatureslowly warming to ambient temperature
  2. waitAfter sixteen hours
  3. customthe reaction was quenched
  4. additionby adding 1N NaOH
  5. extractionextracted with 200 mL of EtOAc
  6. customThe EtOAc layer was separated
  7. washwashed with water
  8. customdried by filtration through anhydrous Na2 SO4, and evaporation to dryness, in vaccuo
  9. customThe crude product was purified by chromatography on a silica gel column
  10. washeluted with EtOAc-hexane (1:4)(v/v)
  11. customThe product was rechromatographed on a silica gel column
  12. washeluted with EtOAc-hexane (1:3)(v/v)

Sources & evidence

ORD record
ord-12023569b2564faeaff1d11d3d8b5fcd
Source dataset
uspto-grants-1998_07
Patent number
US05780648

Reaction notes

Loading…