Lithium borohydride → 2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile

HRID 503908Notes

Reaction equation

HRID 503908 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[CH3:17])[C:8]#[N:9].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]([CH2:6][CH2:5][OH:4])[C:8]#[N:9])=[C:11]([CH3:17])[CH:12]=1

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 668771313-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl esterHCID 86586342KHSO4 Na2SO4

Product 1

HCID 594283342-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrileYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium borohydride (4.99 g, 0.2290 mol) was added to a room temperature solution of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (43.08 g, 0.1527 mol) in THF (500 mL) and the reaction mixture was stirred overnight. The reaction mixture was cooled to 0° C., and a solution of 10% KHSO4/Na2SO4 was slowly added until pH 1-2 was reached. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 27.3 g (87% yield) of 2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile as a white solid.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

Sources & evidence

ORD record
ord-9e7375483a8e47399aedbb2bb604d1d2
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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