4-Chloro-2-fluorobenzyl bromide → HCID 58966910, compound

HRID 1948238Notes

Reaction equation

HRID 1948238 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][N:4]=1.Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[F:27]>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:4]2[CH:5]=[C:6]([CH2:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=[CH:8][C:3]2=[O:2])=[C:21]([F:27])[CH:22]=1

Participants

3

Reactant 2

HCID 27365514-Chloro-2-fluorobenzyl bromideHCID 69344821HCID 69344821, compound

Product 1

HCID 58966910HCID 58966910, compoundYield 48%

Procedure

According to Scheme 22 Step 2: The title compound was prepared according to Example 6 Step 2, from 2-methoxy-5-(3-phenylpropyl)pyridine (1 eq, 0.44 mmol, 0.10 g) and 1-(bromomethyl)-4-chloro-2-fluorobenzene (2 eq, 0.88 mmol, 0.20 g). Reaction conditions: overnight at 90° C. The residue was purified by flash chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 70/30) yielding the title compound (75 mg, 0.21 mmol, 48%) as a yellow oil.

Workup

  1. customThe title compound was prepared
  2. customReaction conditions
  3. customovernight
  4. customat 90° C
  5. customThe residue was purified by flash chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 70/30)

Sources & evidence

ORD record
ord-38ed171f54334af8bbc3e76ac48b258d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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