Sodium borohydride → HCID 13730362, compound

HRID 65460Notes

Reaction equation

HRID 65460 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:6](=[O:9])[CH2:7][Br:8])#[N:2].[BH4-].[Na+].C([BH3-])#N.[Na+].[H][H]>[Pt].[Pd].CO>[Br:8][CH2:7][CH:6]([C:5]1[CH:4]=[C:3]([CH:12]=[C:11]([F:13])[CH:10]=1)[C:1]#[N:2])[OH:9]

Participants

8

Reactant 4

HCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 137303613-Cyano-5-fluorophenacyl bromideHCID 178418361HCID 178418361, compound

Product 1

HCID 13730362HCID 13730362, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

The 3-cyano-5-fluorophenacyl bromide from the above reaction is then dispersed in alcohol, preferably methanol, and reduced with sodium borohydride or sodium cyanoborohydride, or other reducing agents, such as hydrogen and a catalyst, e.g., platinum, palladium, or the like. The reaction yields 3-(2-bromo-1-hydroxyethyl)-5-fluorobenzonitrile which is readily converted to the formula I, 3-[2-(tert-butylamino)-1-hydroxyethyl]-5-fluorobenzonitrile or the 3-fluoro-5-[1-hydroxy-2-(isopropylamino)ethyl]-benzonitrile by reaction with t-butylamine or isopropylamine in the presence of ethanol.

Sources & evidence

ORD record
ord-88767fc2fc3d4a659afec7d93f59cd10
Source dataset
uspto-grants-1986_09
Patent number
US04614746

Reaction notes

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