Sodium borohydride → 4-Fluoro-3-hydroxymethyl-benzonitrile

HRID 1726119Notes

Reaction equation

HRID 1726119 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH:8]=[O:9])#[N:2].[BH4-].[Na+]>CO>[F:11][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:10][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109097255-Cyano-2-fluorobenzaldehyde

Product 1

HCID 431650644-Fluoro-3-hydroxymethyl-benzonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the above aldehyde (5.0 g, 33.5 mmol) in MeOH (330 mL) cooled to 0° C. was added NaBH4 (1.51 g, 40 mmol) and the mixture was stirred at 0° C. for 1 hour. Standard work-up and purification afforded 4-fluoro-3-hydroxymethyl-benzonitrile (4.9 g, 98%) as an off-white solid. 1H NMR (CDCl3) δ 1.95 (br s, 1H), 4.81 (s, 2H), 7.13-7.19 (m, 1H), 7.60-7.62 (m, 1H), 7.83-7.85 (m, 1H).

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-b56961d8c2ab48968b11d4c643e67ca7
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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