Dimethylformamide → 2-(2-bromophenoxy)acetonitrile

HRID 717008Notes

Reaction equation

HRID 717008 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)OCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:10][C:11]#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 27342082-(2-bromophenoxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Into a 50-mL round-bottom flask, was placed 2-bromophenol (5.1 g, 29.48 mmol, 1.00 equiv), 2-bromoacetonitrile (5.3 g, 44.19 mmol, 1.50 equiv), potassium carbonate (8 g, 57.97 mmol, 2.00 equiv), N,N-dimethylformamide (20 mL). The resulting solution was stirred overnight at 60° C. in an oil bath. The resulting solution was diluted with 5×50 mL of EA. The organic layer was washed with 50 mL of H2O. Organic layers were collected and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 6 g (96%) of 2-(2-bromophenoxy)acetonitrile as a brown solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. washThe organic layer was washed with 50 mL of H2O
  3. customOrganic layers were collected
  4. concentrationconcentrated under vacuum
  5. customThis resulted in 6 g (96%) of 2-(2-bromophenoxy)acetonitrile as a brown solid

Sources & evidence

ORD record
ord-c2d81efa8e874fc8acd15c3b2a40dbfb
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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