Dimethylformamide → 5-Formyl-2-hydroxybenzonitrile

HRID 401190Notes

Reaction equation

HRID 401190 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH3:11][N:12](C=O)C>>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([CH:3]=1)[C:11]#[N:12])=[O:6]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 221125485-Formyl-2-hydroxybenzonitrile

Conditions

Temperature
180 °C

Procedure

To a mixture of 3-bromo-4-hydroxybenzaldehyde (1.00 g, 4.97 mmol) in DMF (10 mL) was added cuprous cyanide (660 mg, 7.46 mmol). The mixture was heated at 180° C. for 8 hours. The solution was filtered off and purified by chromatography on silica gel (PE/EtOAc=8:1) (210 mg, 29%).

Workup

  1. filtrationThe solution was filtered off
  2. custompurified by chromatography on silica gel (PE/EtOAc=8:1) (210 mg, 29%)

Sources & evidence

ORD record
ord-1162f9caeb1b44ea958e9204a0855c37
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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