Methanol → Benzonitrile, m-chloro-

HRID 76864

Reaction equation

HRID 76864 reaction equation
[Si](OCCC1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)(C(C)(C)C)(C)C.BrC[C:37]1[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][C:38]=1[Cl:45].CO.N(CC)CC>CC#N>[Cl:45][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:37]=1)[C:41]#[N:42]

Participants

6

Reactant 4

HCID 887MethanolHCID 8021DiethylamineHCID 130420934-(Bromomethyl)-3-chlorobenzonitrileHCID 668853594-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1-trityl-1H-imidazole

Product 1

HCID 13015Benzonitrile, m-chloro-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1-trityl-1H-imidazole (3.98 g, 8.5 mmol) and 4-bromomethyl-3-chlorobenzonitrile (2.93 g, 12.7 mmol) are dissolved in MeCN (40 mL) and heated at 80° C. for 5 h. After cooling to room temperature MeOH (40 mL) and Et2NH (7 mL) are then added and the solution is warmed 70° C. for 1 h. The solution is evaporated to dryness and the residue purified via flash column chromatography (acetone/CH2Cl2 1:3→MeOH/CH2Cl2 5:95) to give 4-{5-[2-tert-butyl-dimethylsilanyloxy)ethyl]-imidazol-1-ylmethyl}-3-chlorobenzonitrile as an oil. MS (ESI) m/z 376.3, 378.3 (M+H).

Workup

  1. additionare then added
  2. temperaturethe solution is warmed 70° C. for 1 h
  3. customThe solution is evaporated to dryness
  4. customthe residue purified via flash column chromatography (acetone/CH2Cl2 1:3→MeOH/CH2Cl2 5:95)

Sources & evidence

ORD record
ord-79cdbd8def654cd999b2d85bcce979ca
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Linked notes

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