Triphenylphosphine → HCID 69344889, compound

HRID 1948266Notes

Reaction equation

HRID 1948266 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:21])=[CH:4][CH:3]=1.C1C(=O)N([Br:31])C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][Br:31])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:8]2=[O:21])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 69349174HCID 69349174, compound

Product 1

HCID 69344889HCID 69344889, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 25 Step 3: To a solution of 1-(4-chlorobenzyl)-5-(4-(hydroxymethyl)phenyl)pyridin-2(1H)-one (1 eq, 3.07 mmol, 1.00 g, Example 35 Step 1) in THF (8 mL) were added NBS (1.22 eq, 3.74 mmol, 0.67 g) and PPh3 (1.20 eq, 3.68 mmol, 0.97 g) at −20° C. for 4 hours. After evaporation of the solvent, the crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 50 g SiO2) using CH2Cl2/MeOH 98/2 to afford 1-(4-chlorobenzyl)-5-(4-(bromomethyl)phenyl)pyridin-2(1H)-one (2.06 mmol, 0.80 g, 67%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 50 g SiO2)

Sources & evidence

ORD record
ord-ef6e602b30544efaa324874bb8d56b3e
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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