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

HRID 1493490Notes

Reaction equation

HRID 1493490 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-d0ca1c54e85e461a947f76f91105a088
Source dataset
uspto-grants-1991_06
Patent number
US05021581

Reaction notes

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