6-Bromo-3-benzofuranacetonitrile → HCID 57192363, compound

HRID 1459416Notes

Reaction equation

HRID 1459416 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][C:10]#[N:11])=[CH:7][O:8][C:4]=2[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 847979636-Bromo-3-benzofuranacetonitrile

Product 1

HCID 57192363HCID 57192363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11-6 (10.9 g, 0.0462 mol) in THF (100 mL) was cooled to 0° C. and treated dropwise with BH3 /THF solution (1Molar, 110.8 mL, 0.11 mol). The cold bath was removed and the reaction stirred overnight. MeOH was carefully added (20 mL) and the solvent removed under vacuum. The residue was dissolved in 50 mL MeOH and 400 mL MeOH saturated with HCl and heated to reflux for 3 hours. The volatile components were removed under vacuum and the residue was suspended in Et2O. A bright yellow solid percipitated and was collected and washed five times with Et2O, then dried under vacuum to give 11-7 as a tan solid.

Workup

  1. customThe cold bath was removed
  2. additionMeOH was carefully added (20 mL)
  3. customthe solvent removed under vacuum
  4. dissolutionThe residue was dissolved in 50 mL MeOH
  5. temperature400 mL MeOH saturated with HCl and heated
  6. temperatureto reflux for 3 hours
  7. customThe volatile components were removed under vacuum
  8. customA bright yellow solid percipitated and was collected
  9. washwashed five times with Et2O
  10. customdried under vacuum

Sources & evidence

ORD record
ord-a9fd2a6783df4b84b0c95c92aca448b9
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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