Sodium borohydride → 2-Cyano-3-(6-bromo-2,3-dimethoxyphenyl)-propionic acid

HRID 2290918Notes

Reaction equation

HRID 2290918 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:9]=1[O:17][CH3:18])[C:4]([OH:6])=[O:5])#[N:2].[BH4-].[Na+]>CCO>[C:1]([CH:3]([CH2:7][C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:9]=1[O:17][CH3:18])[C:4]([OH:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53869906alpha-Cyano-6-bromo-2,3-dimethoxycinnamic acid

Product 1

HCID 127893842-Cyano-3-(6-bromo-2,3-dimethoxyphenyl)-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of α-cyano-6-bromo-2,3-dimethoxycinnamic acid (41.7 g, 0.13 mole), and absolute EtOH (1 L) was stirred under N2 at 0° as NaBH4 (42 g. 1.11 mole) was added portionwise. The reaction mixture was stirred at room temperature for 0.5 hr., and at reflux for 0.75 hr. After cooling to room temperature, EtOH was removed (in-vacuo). Water was added to the residue, followed by 10% HCl until acidic. The solution was extracted with CH2Cl2. The combined organic layers were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 39.25 g cream colored solid; mp 120°-2°; M+ 313.

Workup

  1. additionwas added portionwise
  2. temperature, and at reflux for 0.75 hr
  3. temperatureAfter cooling to room temperature
  4. customEtOH was removed (in-vacuo)
  5. additionWater was added to the residue
  6. extractionThe solution was extracted with CH2Cl2
  7. washThe combined organic layers were washed with water, saturated aqueous NaCl
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto yield 39.25 g cream colored solid

Sources & evidence

ORD record
ord-9d3158be250d4132bd93af73c96f402a
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

Loading…