Benzaldehyde, 2-hydroxy-5-methyl- → 2-(5-Methylbenzofuran-2-yl)benzonitrile

HRID 1034436Notes

Reaction equation

HRID 1034436 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=O.C[O-].[Na+].Br[CH2:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN(C=O)C.C(O)C>[CH3:10][C:7]1[CH:8]=[CH:9][C:2]2[O:1][C:15]([C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[CH:4][C:3]=2[CH:6]=1

Participants

6

Reactant 3

HCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 895992-(Bromomethyl)benzonitrileHCID 10942334Sodium Methoxide2×

Product 1

HCID 156808442-(5-Methylbenzofuran-2-yl)benzonitrileYield 68.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
75 °C

Procedure

A solution of the product of step (a) (130 g) in dry DMF (400 ml) was added dropwise to a solution of sodium methoxide (56.2 g) in ethanol (400 ml) mechanically stirred under nitrogen. After 20 mins, a solution of 2-(bromomethyl)benzonitrile (182.2 g) in dry DMF (400 ml) was added dropwise. The mixture was then heated to 75° C. for 30 min. The solution was allowed to cool for 1 h. A slurry of sodium methoxide (56.2 g) in dry DMF (100 ml) was added and the mixture heated at reflux for 1.5 h. The mixture was concentrated in vacuo and then poured into iced water. The solid was collected, and then triturated with methanol to give the title compound (Intermediate 2) as a beige solid (149.4 g).

Workup

  1. temperatureto cool for 1 h
  2. temperaturethe mixture heated
  3. temperatureat reflux for 1.5 h
  4. concentrationThe mixture was concentrated in vacuo
  5. additionpoured into iced water
  6. customThe solid was collected
  7. customtriturated with methanol

Sources & evidence

ORD record
ord-dd2e13a5f47143f3a2d6a0370a3de0f8
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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