Methyl 4-(bromomethyl)-3-chlorobenzoate → Methyl 3-chloro-4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzoate

HRID 2186045Notes

Reaction equation

HRID 2186045 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[Cl:13].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[C:14]1(=[O:24])[N:18]([CH2:2][C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=2[Cl:13])[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12

Participants

4

Reactant 2

HCID 22027761Methyl 4-(bromomethyl)-3-chlorobenzoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 22451715Methyl 3-chloro-4-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 4-bromomethyl-3-chlorobenzoate 10 g, 38 mmol) and potassium phthalimide (9.85 g, 53 mmol) in dimethylformamide (65 mL) was stirred and heated to 85° C. for 2 h. The hot mixture was poured into ice water and the resulting solid was filtered, washed sequentially with water, ethanol and a small amount of ether and dried to give the title compound.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed sequentially with water, ethanol
  3. dry with materiala small amount of ether and dried

Sources & evidence

ORD record
ord-e1b64eb5c6974cd9b8f96fea8b134ce1
Source dataset
uspto-grants-2002_06
Patent number
US06403578B1

Reaction notes

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