Sodium Cyanide → 4-Bromo-2-cyanomethylphenyl benzyl ether

HRID 355805Notes

Reaction equation

HRID 355805 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:18]#[N:19].[Na+]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8929Sodium Cyanide2×HCID 117832201-(Benzyloxy)-4-bromo-2-(bromomethyl)benzene

Product 1

HCID 226754674-Bromo-2-cyanomethylphenyl benzyl etherYield 56.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromomethyl-4-bromophenyl benzyl ether (0.28 moles) and NaCN (16 g) in DMF (200 ml) was stirred at ambient temperature for 16 hours, then heated at 100° C. for 5 hours. A further 2 g of NaCN was added and the reaction heated for 5 hours at 100° C. The mixture was diluted with water (200 ml) and stirred (1 hour). The resulting solid was filtered off and recrystallised from methanol to give 4-bromo-2-cyanomethylphenyl benzyl ether (48 g) mpt. 75°-76° C.

Workup

  1. temperatureheated at 100° C. for 5 hours
  2. temperaturethe reaction heated for 5 hours at 100° C
  3. stirringstirred (1 hour)
  4. filtrationThe resulting solid was filtered off
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-bc03b3025d01401e8be5a108ddc22102
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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