4-Chloro-2-fluorobenzyl bromide → HCID 58966958, compound

HRID 1948256Notes

Reaction equation

HRID 1948256 reaction equation
C[O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:5][N:4]=1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[F:28]>C(#N)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:4]2[CH:5]=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:7]=[C:8]([O:9][CH3:10])[C:3]2=[O:2])=[C:22]([F:28])[CH:23]=1

Participants

4

Reactant 2

HCID 27365514-Chloro-2-fluorobenzyl bromideHCID 693449082,3-Dimethoxy-5-(4-methoxyphenyl)pyridine

Product 1

HCID 58966958HCID 58966958, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 4 Step 1: The title compound was prepared from 2,3-dimethoxy-5-(4-methoxyphenyl)pyridine (1 eq, 0.41 mol, 0.10 g) and 1-(bromomethyl)-4-chloro-2-fluorobenzene (2 eq, 0.82 mmol, 0.18 g) according to the procedure described for Example 6 Step 2. Reaction conditions: 14 hours at 80° C. in acetonitrile. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2) using cyclohexane/AcOEt 70/30 to 50/50 as eluent to afford 1-(4-Chloro-2-fluorobenzyl)-3-methoxy-5-(4-methoxyphenyl)pyridin-2(1H)-one (0.24 mmol, 0.09 g, 59%).

Workup

  1. customReaction conditions
  2. custom14 hours
  3. customat 80° C.
  4. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-559f59ba080445e490d563bb77fbe3c6
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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