Water → 2-[(3-Chlorophenoxy)methyl]benzonitrile

HRID 480551Notes

Reaction equation

HRID 480551 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 142553142-[(3-Chlorophenoxy)methyl]benzonitrileYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-chlorophenol (9.26 g) in DMF (25 ml) was added dropwise to a stirred suspension of sodium hydride (1.44 g) in DMF (50 ml) (effervescence) and the resulting mixture was stirred at room temperature for 1 hour. A solution of 2-(bromomethyl)benzonitrile (11.76 g) in DMF (25 ml) was then added to the stirred reaction mixture and after a further hour at room temperature the mixture was poured into water and extracted with ether. The extracts were washed successively with water, dilute aqueous sodium hydroxide and brine, then dried and concentrated to give crude 2-(3-chlorophenoxymethyl)-benzonitrile (13.95 g) as an orange-brown oil which crystallised on standing. An analytical sample, recrystallised from petrol, had m.p. 56° C.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed successively with water, dilute aqueous sodium hydroxide and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d06442f19984e10b1920811816a5168
Source dataset
uspto-grants-2003_11
Patent number
US06653258B1

Reaction notes

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