Carbon tetrabromide → 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one

HRID 591768Notes

Reaction equation

HRID 591768 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:24])[NH:5][C:6]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([O:19][CH2:20][CH2:21]O)=[C:14]([CH3:23])[CH:13]=1)=[N:7]2.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:26][CH2:21][CH2:20][O:19][C:15]1[C:16]([CH3:18])=[CH:17][C:12]([C:6]2[NH:5][C:4](=[O:24])[C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[Cl:1])[N:7]=2)=[CH:13][C:14]=1[CH3:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1361833855-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

Product 1

HCID 1364150762-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-oneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one (0.40 g, 1.16 mmol) in anhydrous DMF (10 mL) was added carbon tetrabromide (0.42 g, 1.27 mmol) and triphenylphosphine (0.33 g, 1.27 mmol). The reaction mixture was stirred at room temperature for 27 hours. Solvent was evaporated to dryness in vacuo and the residue triturated with Et2O (15 mL)/EtOAc (15 mL) to give 2-(4-(2-bromoethoxy)-3,5-dimethylphenyl)-5-chloroquinazolin-4(3H)-one (0.42 g). It was used without further purification. The 1H NMR indicated a purity of about 45%.

Workup

  1. customSolvent was evaporated to dryness in vacuo
  2. customthe residue triturated with Et2O (15 mL)/EtOAc (15 mL)

Sources & evidence

ORD record
ord-ea6f020bd720458293f4903fe42d477f
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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