Boron tribromide → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dihydroxy-benzonitrile

HRID 1186033Notes

Reaction equation

HRID 1186033 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:20]=[C:19]([O:21]C)[C:18]([O:23]C)=[CH:17][C:14]=1[C:15]#[N:16].B(Br)(Br)Br>C(Cl)Cl>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][C:13]1[CH:20]=[C:19]([OH:21])[C:18]([OH:23])=[CH:17][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 671887662-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dimethoxy-benzonitrile

Product 1

HCID 582456992-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dihydroxy-benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dimethoxy-benzonitrile (20.36 g, 0.0632 mol) was dissolved in warm methylene chloride (253 mL) then cooled to 0° C. Boron tribromide (1 M in CH2Cl2, 253 mL, 0.2527 mol) was added dropwise over 45 min while maintaining the temperature under 5° C., under nitrogen. The resulting mixture was allowed to warm to room temperature with stirring under nitrogen for 23 h. The resulting mixture was then cooled to 0° C. and quenched by the dropwise addition of methanol (90 mL) over 45 min. The resulting mixture was concentrated in vacuo. The resulting precipitate was suspended in methanol (2×) and concentrated in vacuo. The resulting precipitate was taken up in boiling methanol (900 mL) and hot filtered. The filtrate was concentrated to about 200 mL and allowed to crystallize. The resulting precipitate was collected via filtration to yield the title compound-2-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,5-dihydroxy-benzonitrile—as a gray solid.

Workup

  1. temperaturewhile maintaining the temperature under 5° C.
  2. temperatureto warm to room temperature
  3. temperatureThe resulting mixture was then cooled to 0° C.
  4. customquenched by the dropwise addition of methanol (90 mL) over 45 min
  5. concentrationThe resulting mixture was concentrated in vacuo
  6. concentrationconcentrated in vacuo
  7. concentrationThe filtrate was concentrated to about 200 mL
  8. customto crystallize
  9. filtrationThe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-c78aa9b03a884474b620cfaab87a4f12
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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