3-Fluorobenzyl bromide → HCID 22049898, compound

HRID 1948213Notes

Reaction equation

HRID 1948213 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][C:2]=1[OH:8].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1>CN(C=O)C>[F:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][N:1]1[CH:6]=[CH:5][C:4]([O:7][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:3][C:2]1=[O:8]

Participants

4

Reactant 2

HCID 680073-Fluorobenzyl bromideHCID 178516518HCID 178516518, compound

Product 1

HCID 22049898HCID 22049898, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Scheme 13 Step 1: The title compound was prepared from pyridine-2,4-diol (1 eq, 2.52 mmol, 0.28 g) and 1-(bromomethyl)-3-fluorobenzene (3 eq, 7.56 mmol, 0.93 mL) according to the procedure described for Example 1 Step 2. Reaction conditions: 17 h under reflux in DMF. The crude product was purified by flash chromatography on silica gel (CH2Cl2/AcOEt 90/10) to afford 1-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)pyridin-2(1H)-one as a white solid (0.95 mmol, 0.29 g, 36%).

Workup

  1. customReaction conditions
  2. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/AcOEt 90/10)

Sources & evidence

ORD record
ord-1d72061226544d9792b964495cde5380
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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