4-Methoxybenzyl alcohol → HCID 59496811, compound

HRID 417045Notes

Reaction equation

HRID 417045 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.[H-].[Na+].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20](Br)[CH:21]=1)[C:17]#[N:18]>CN(C=O)C.C(OCC)(=O)C>[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:21]=1)[C:17]#[N:18]

Participants

6

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydride2×HCID 27976903,5-Dibromobenzonitrile

Product 1

HCID 59496811HCID 59496811, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

p-Methoxybenzyl alcohol (2.6 mL) was dissolved in anhydrous DMF (50 mL) and NaH (808 mg, 60% dispersion in oil) was added in several portions. After gas evolution ceased, 3,5-dibromobenzonitrile (5.0 g) was added and the reaction mixture was stirred at 70° C. After 2 h additional amount of NaH (147 mg) was added and heating was continued for 6 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 3.1 g of the title compound (51% yield). HRMS calcd for C15H12O2BrN M+ 371.0051, observed 371.0048.

Workup

  1. temperatureheating
  2. washwashed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-b8eef65b59ea45d0be060941182f124d
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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