Carbon tetrabromide → 2-[4-(2-bromo-ethoxy)-3,5-dimethylphenyl]-5,7-dichloro-3H-quinazolin-4-one

HRID 591719Notes

Reaction equation

HRID 591719 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[NH:5][C:6]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([O:20][CH2:21][CH2:22]O)=[C:15]([CH3:24])[CH:14]=1)=[N:7]2.C(Br)(Br)(Br)[Br:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[Br:27][CH2:22][CH2:21][O:20][C:16]1[C:17]([CH3:19])=[CH:18][C:13]([C:6]2[NH:5][C:4](=[O:25])[C:3]3[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=3[Cl:1])[N:7]=2)=[CH:14][C:15]=1[CH3:24]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1360380035,7-dichloro-2-[4-(2-hydroxy-ethoxy)-3,5-dimethylphenyl]-3H-quinazolin-4-one

Product 1

HCID 1363480352-[4-(2-bromo-ethoxy)-3,5-dimethylphenyl]-5,7-dichloro-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5,7-dichloro-2-[4-(2-hydroxy-ethoxy)-3,5-dimethylphenyl]-3H-quinazolin-4-one (1.14 g, 3.00 mmol) in anhydrous DMF (15 mL) was added carbon tetrabromide (1.10 g, 3.30 mmol). Then, triphenylphosphine (0.86 g, 3.30 mmol) was added in small portions. The reaction mixture was stirred at room temperature for 16 hours under nitrogen. Solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate (50 mL) and dried under vacuum to give 2-[4-(2-bromo-ethoxy)-3,5-dimethylphenyl]-5,7-dichloro-3H-quinazolin-4-one as a white solid. Yield: 0.46 g (35%).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. washThe residue was washed with ethyl acetate (50 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-838ba69b03fa4b6c9b70ae105f593ddf
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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