Hydrochloric Acid → 2,5-Difluoro-4-(hydroxymethyl)benzonitrile

HRID 1717501Notes

Reaction equation

HRID 1717501 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5].[BH4-].[Na+].O.Cl>CO>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 219046262,5-Difluoro-4-formylbenzonitrile

Product 1

HCID 219046532,5-Difluoro-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-Difluoro-4-formylbenzonitrile (3.60 g, 0.0215 mol; see step (ii) above) was dissolved in 50 mL of methanol and cooled on an ice bath. Sodium borohydride (0.815 g, 0.0215 mol) was added in portions with stirring and the reaction was left for 45 min. Water (300 mL) was added and thereafter carefully 2M HCl was added until an acidic pH was attained. The mixture was extracted three times with diethyl ether, and the combined ethereal phase washed with water, dried (Na2SO4) and evaporated. The crude product crystallised soon and could be used without further purification. Yield: 3.1 g (85%).

Workup

  1. temperaturecooled on an ice bath
  2. extractionThe mixture was extracted three times with diethyl ether
  3. washthe combined ethereal phase washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product crystallised soon
  7. customcould be used without further purification

Sources & evidence

ORD record
ord-d1585aff04834504b1c2015a22410459
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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