4-Chloro-2-fluorobenzyl bromide → HCID 58966916, compound

HRID 1948272Notes

Reaction equation

HRID 1948272 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[C:6]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][N:4]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[F:29]>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:4]2[CH:5]=[C:6]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:7]([CH2:9][O:10][CH3:11])=[CH:8][C:3]2=[O:2])=[C:23]([F:29])[CH:24]=1

Participants

3

Reactant 2

HCID 27365514-Chloro-2-fluorobenzyl bromideHCID 69345451HCID 69345451, compound

Product 1

HCID 58966916HCID 58966916, compoundYield 1%

Procedure

According to Scheme 31 Step 4: The title compound was prepared from 2-methoxy-4-(methoxymethyl)-5-(4-methoxyphenyl)pyridine (1 eq, 0.66 mmol, 0.17 g) and 1-(bromomethyl)-4-chloro-2-fluorobenzene (1.5 eq, 0.98 mmol, 0.22 g) according to the procedure described for Example 6 Step 2. Reaction conditions: 12 hours at 80° C. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 98/2 as the eluent to afford 1-(4-chloro-2-fluorobenzyl)-4-(methoxymethyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (5 μmol, 2 mg, 1%) as yellow oil.

Workup

  1. customReaction conditions
  2. custom12 hours
  3. customat 80° C
  4. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-0952f781e32444c889331ac7b64fc4e9
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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