4-(Bromomethyl)-1-chloro-2-methoxybenzene → HCID 22467651, compound

HRID 1934709Notes

Reaction equation

HRID 1934709 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=1[O:10][CH3:11].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:16]2[C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]3[C:12]2=[O:22])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 22467651HCID 22467651, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-methoxybenzyl bromide (7.00 g) in anhydrous dimethylformamide (50 mL) was added potassium phthalimide (6.03 g), and the mixture was stirred for 2 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give N-(4-chloro-3-methoxybenzyl)phthalimide as white powders (5.88 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-1b00eb601bb54029bd7a3c61741b8537
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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