4-(Bromomethyl)benzonitrile → HCID 54160280, compound

HRID 443229Notes

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

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 furthur 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

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

Sources & evidence

ORD record: ord-0c9b1c59d4674956bfcd606d104b7072
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891889

Reaction notes

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