4-(Bromomethyl)benzonitrile → HCID 54160280, compound

HRID 1068409Notes

Reaction equation

HRID 1068409 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:40]([C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Br)=[CH:44][CH:43]=1)#[N:41]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:5]1[N:6]=[CH:7][N:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)[CH2:46][C:45]1[CH:48]=[CH:49][C:42]([C:40]#[N:41])=[CH:43][CH:44]=1

Participants

5

Reactant 3

HCID 869964-(Bromomethyl)benzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Product 1

HCID 54160280HCID 54160280, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 1-(triphenylmethyl)-1H-imidazol-4-ylacetic acid methyl ester (977 mg, 2.55 mmol) in THF (25 ml) was cooled to −78° C. Lithium hexamethyldisilazide (2.68 ml, 2.68 mmol) was added dropwise and the reaction stirred 30 min at −78° C. 4-Cyanobenzyl bromide (500.7 mg, 2.68 mmol) was added and the reaction stirred a further 4 hrs at −78° C. and then at −20° C. for 12 hr. The reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml) and extracted with EtOAc. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product.

Workup

  1. stirringthe reaction stirred a further 4 hrs at −78° C.
  2. waitat −20° C. for 12 hr
  3. customThe reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customChromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product

Sources & evidence

ORD record
ord-3026a9bf3ea84d2e848b17242575bbf8
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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