1-(Bromomethyl)-4-chlorobenzene → 5-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-one

HRID 1948189Notes

Reaction equation

HRID 1948189 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1>O>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]2=[O:8])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 603727735-Bromo-1-[(4-chlorophenyl)methyl]-1,2-dihydropyridin-2-oneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to Scheme 1 Step 2: The title compound was prepared from 5-bromopyridin-2(1H)-one (1 eq, 29.0 mmol, 5.00 g, Example 1 Step 1) and 4-chlorobenzyl bromide (1.2 eq, 34.0 mmol, 7.10 g) according to the procedure described for Example 1 Step 2. After concentration of the solvent, water was added. The aqueous phase was extracted with AcOEt and the combined organic fractions were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was recrystallized with pentane/Et2O 50/50 to afford 1-(4-chlorobenzyl)-5-bromopyridin-2(1H)-one (26.2 mmol, 7.82 g, 91%) as a white solid.

Workup

  1. extractionThe aqueous phase was extracted with AcOEt
  2. dry with materialthe combined organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was recrystallized with pentane/Et2O 50/50

Sources & evidence

ORD record
ord-103bfdafba8a48fa8924477ea639f154
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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