4-(Bromomethyl)benzonitrile → HCID 54021566, compound

HRID 342155Notes

Reaction equation

HRID 342155 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][N:13](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=1>C(#N)C>[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=2)[CH:12]=[N:13][CH:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 618241HCID 618241, compound

Product 1

HCID 54021566HCID 54021566, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(tert-butyldimethylsilyloxymethyl)-1-triphenylmethylimidazole (4.66 g, 10.26 mmol) and 1-bromomethyl-4-cyanobenzene (2.01 g, 10.26 mmol) in acetonitrile (50 mL) was refluxed 4 h. The reaction was cooled, acetonitrile removed in vacuo, and the residue dissolved in methanol (30 mL). This solution was refluxed for 2 h, cooled and methanol evaporated. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The crude product was chromatographed on silica with 3% methanol in chloroform. The title compound was obtained as a white solid.

Workup

  1. temperatureThe reaction was cooled
  2. customacetonitrile removed in vacuo
  3. dissolutionthe residue dissolved in methanol (30 mL)
  4. temperatureThis solution was refluxed for 2 h
  5. temperaturecooled
  6. custommethanol evaporated
  7. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  8. customThe crude product was chromatographed on silica with 3% methanol in chloroform

Sources & evidence

ORD record
ord-57f34b8dac5f42e7b8e82774e7177843
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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