2-Bromomethylnaphthalene → HCID 178478239, compound

HRID 922612Notes

Reaction equation

HRID 922612 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[C:16]([Cl:17])=[C:15]([Cl:18])[N:14]=[CH:13]1.[Br:19][CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1>C(#N)C>[Br-:19].[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N+:12]1[C:16]([Cl:17])=[C:15]([Cl:18])[N:14]([CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 703202-BromomethylnaphthaleneHCID 70982063HCID 70982063, compound

Product 1

HCID 178478239HCID 178478239, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Benzo[1,4]dioxan-2-ylmethyl)-4,5-dichloroimidazole (0.28 g, 1 mmol) was combined with acetonitrile (2 mL) and heated until all solid dissolved. 2-(Bromomethyl)naphthalene (0.22 g, 1 mmol) was added and the solution was refluxed for 3 h, during which time a white precipitate formed. The precipitate was collected by filtration and washed with diethyl ether to yield a white solid (0.29 g, 57% yield). 1H NMR (300 MHz, DMSO-d6) 9.65 (1H, s, NCHN), 8.00 (4H, m, Ar), 7.57 (3H, m, Ar), 6.87 (4H, m, Ar), 5.72 (2H, s, CH2), 4.11-4.88 (5H, m, CH2CHCH2O).

Workup

  1. temperatureheated until all solid
  2. dissolutiondissolved
  3. temperaturethe solution was refluxed for 3 h, during which time a white precipitate
  4. customformed
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-efe4e335a6134c07bb5236924ab5cb97
Source dataset
uspto-grants-2016_03
Patent number
US09278951B2

Reaction notes

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