4-(Bromomethyl)-1,2-difluorobenzene → HCID 58966905, compound

HRID 1948225Notes

Reaction equation

HRID 1948225 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][N:4]=1.Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1>CN(C=O)C>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[F:25])[CH2:18][N:4]1[CH:5]=[C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][C:3]1=[O:2]

Participants

4

Reactant 2

HCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 58483799HCID 58483799, compound

Product 1

HCID 58966905HCID 58966905, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to Scheme 16 Method A: The title compound was prepared from 2-methoxy-5-(phenoxymethyl)pyridine (1 eq, 0.46 mmol, 0.10 g) and 4-(bromomethyl)-1,2-difluorobenzene (3 eq, 1.39 mmol, 0.18 mL) according to the procedure described for Example 1 Step 2. Reaction conditions: under reflux for 3 days in DMF (5 mL). The crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/AcOEt 90/10 followed by recrystallization in diisopropyl ether to afford 1-(3,4-difluorobenzyl)-5-(phenoxymethyl)pyridin-2(1H)-one (0.14 mmol, 0.04 g, 29%) as a white solid.

Workup

  1. customReaction conditions
  2. customThe crude oil was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 25 g SiO2)
  3. customfollowed by recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-6c6be745bcd342cab0baf7c8ccb2ce4d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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