2-Methoxyethanol → HCID 24702676, compound

HRID 219901Notes

Reaction equation

HRID 219901 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].C(N(C(C)C)C(C)C)C.[CH3:20][O:21][CH2:22][CH2:23][OH:24]>CCOC(C)=O>[CH3:20][O:21][CH2:22][CH2:23][O:24][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 81531DiisopropylethylamineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 24702676HCID 24702676, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(bromomethyl)benzonitrile (1 g, 5.1 mmol) in 2-methoxyethanol (10 mL) and n-ethyldiisopropylamine (0.89 mL, 5.1 mmol) was heated under microwave irradiations for 2 hours at 150° C. After this time, reaction mixture was diluted with EtOAc (200 mL), washed with water and brine to give the title compound as a colorless oil (800 mg, 81%). 1H NMR (DMSO-d6, 300 MHz) δ 7.76-7.74 (m, 2H), 7.68-7.65 (m, 1H), 7.59-7.54 (m, 1H), 4.54 (s, 2H), 3.59-3.56 (m, 2H), 3.51-3.47 (m, 2H), 3.25 (s, 3H). HPLC (Method A) Rt 3.09 min (Purity: 82.9%).

Workup

  1. customAfter this time, reaction mixture
  2. washwashed with water and brine

Sources & evidence

ORD record
ord-82276b266d4943ceb01b695d06f309ee
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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