Trifluoroacetic acid → 3-Benzyl-5-bromopyridin-4-one

HRID 1364375Notes

Reaction equation

HRID 1364375 reaction equation
[Br:1][CH:2]1[C:7](=[O:8])[C:6]([CH:9](O)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][N:4]=[CH:3]1.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>ClCCl>[CH2:9]([CH:6]1[C:7](=[O:8])[C:2]([Br:1])=[CH:3][N:4]=[CH:5]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 669368273-Bromo-5-(hydroxy-phenyl-methyl)-pyridin-4-one

Product 1

HCID 669366583-Benzyl-5-bromopyridin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-5-(hydroxyl-phenyl-methyl)pyridin-4-one 11 (0.125 g, 91 mmol), TFA (16 mL) and Et3SiH in anhydrous dichloromethane (30 mL) was stirred at rt for 10 h [Borzilleri, et al., U.S. Pat. 20050245530]. The reaction mixture was concentrated in vacuo and the residue purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2). Yield 0.081 g (69%), white solid. 1H NMR (MeOH— d4, 500 MHz): δ 8.12 (s, 1H), 7.47 (s, 1H), 7.29-7.17 (m, 5H), 3.83 (s, 2H). 13C NMR (MeOH—d4, 125 MHz): δ 175.2, 140.7, 139.5, 136.9, 130.8, 130.0, 130.0, 129.5, 129.5, 127.3, 114.1, 34.9.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by flash column chromatography on silica gel (dichloromethane:methanol, 98:2)

Sources & evidence

ORD record
ord-33de683d9a68457bb7f02cbd0773b09c
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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