Sodium borohydride → HCID 67439549, compound

HRID 1255610Notes

Reaction equation

HRID 1255610 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[Cl:15])=[CH:4][C:3]=1[CH:18]=[O:19].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[Cl:15])=[CH:4][C:3]=1[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86636410HCID 86636410, compound

Product 1

HCID 67439549HCID 67439549, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-bromo-3-formylphenoxy)-3-chlorobenzonitrile (9.25 g, 27.4 mmol) in methanol (80 mL) was added sodium borohydride (522 mg, 13.7 mmol) portionwise at 0° C., and the mixture was stirred at room temperature for 1 h. The solvent was removed to about a half volume, 1 M HCl was added, and the mixture was poured into ethyl acetate/water. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (8:2 to 7:3 hexane/ethyl acetate) to give 4-(4-bromo-3-(hydroxymethyl)phenoxy)-3-chlorobenzonitrile (8.19 g, 3 steps, 85%).

Workup

  1. customThe solvent was removed to about a half volume, 1 M HCl
  2. additionwas added
  3. additionthe mixture was poured into ethyl acetate/water
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel chromatography (8:2 to 7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8f8f84a10e494501aeab4677dad8d36a
Source dataset
uspto-grants-2013_06
Patent number
US08461135B2

Reaction notes

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