Hydrochloric Acid → 3-Fluoro-4-hydroxymethylbenzonitrile

HRID 2090196Notes

Reaction equation

HRID 2090196 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5]([F:13])[CH:4]=1)#[N:2].[BH4-].[Na+].Cl>CO>[F:13][C:5]1[CH:4]=[C:3]([CH:12]=[CH:11][C:6]=1[CH2:7][OH:8])[C:1]#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15278726Methyl 4-cyano-2-fluorobenzoate

Product 1

HCID 114805433-Fluoro-4-hydroxymethylbenzonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.10 g (89.9 mmol) of methyl 4-cyano-2-fluorobenzoate are dissolved in 150 ml of methanol. Then 3.40 g (89.9 mmol) of sodium borohydride are added in portions. After the reaction has taken place (TLC check), the mixture is adjusted to pH 3 with dilute hydrochloric acid and extracted several times with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution and dried with magnesium sulfate. The solvent is then removed in vacuo, and the residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 15:1→3:7). 3.70 g (27.2% of theory) of the title compound are obtained.

Workup

  1. extractionextracted several times with dichloromethane
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent is then removed in vacuo
  5. customthe residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 15:1→3:7)

Sources & evidence

ORD record
ord-6c420f70b5de4e4189efa96cfa130465
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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