Benzonitrile, 3-(bromomethyl)- → 3-[(2-Hydroxyethoxy)methyl]benzonitrile

HRID 219902Notes

Reaction equation

HRID 219902 reaction equation
O[N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][CH2:13][CH2:14][O:15]C)[CH:6]=1)N.BrCC1C=C(C=CC=1)C#N>C(O)CO>[OH:15][CH2:14][CH2:13][O:12][CH2:11][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:3]#[N:2]

Participants

4

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 74313394N'-hydroxy-3-[(2-methoxyethoxy)methyl]benzenecarboximidamide

Product 1

HCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

The title compound was obtained following procedure described for Intermediate 75 but starting from 3-(bromomethyl)benzonitrile (1 g, 5.1 mmol) and ethylene glycol (10 mL) to give the title compound as a yellowish oil. 1H NMR (DMSO-d6, 300 MHz) δ 7.80 (bs, 1H), 7.76-7.74 (m, 2H), 7.69-7.67 (m, 1H), 7.59-7.53 (m, 1H), 4.68 (t, J=5.4 Hz, 1H), 4.55 (s, 2H), 3.58-3.53 (m, 2H), 3.50-3.46 (m, 2H). HPLC (Method A) Rt 2.31 min (Purity: 83.5%).

Sources & evidence

ORD record
ord-2dcad39b29e649d8b44d6a5e3c5aa7d8
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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