1-(Bromomethyl)-4-chlorobenzene → HCID 69350494, compound

HRID 1948250Notes

Reaction equation

HRID 1948250 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1>C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:6]2[CH:7]=[C:2]([Br:1])[N:3]=[CH:4][C:5]2=[O:8])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 27716182-Bromo-5-hydroxypyrazine

Product 1

HCID 69350494HCID 69350494, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 27 Step 1: The title compound was prepared from 5-bromopyrazin-2(1H)-one (1 eq, 2.86 mmol, 0.50 g) and 1-(bromomethyl)-4-chlorobenzene (1.5 eq, 4.29 mmol, 0.88 g) according to the procedure described for Example 1 Step 2. Reaction conditions: 3 hours at 70° C. in acetonitrile. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using pure AcOEt as eluent to afford 1-(4-chlorobenzyl)-5-bromopyrazin-2(1H)-one (2.48 mmol, 0.74 g, 87%) as a white solid.

Workup

  1. customReaction conditions
  2. custom3 hours
  3. customat 70° C.
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-324b206e1ccd48708be64594c9618657
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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