N-bromobutanimide → 7-Amino-8-bromo-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

HRID 14476Notes

Reaction equation

HRID 14476 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[C:8]([CH:12]([CH3:14])[CH3:13])[O:9]2)=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]([Br:23])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)=[C:8]([CH:12]([CH3:13])[CH3:14])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 116811907-Amino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Product 1

HCID 597242447-Amino-8-bromo-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 7-amino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (0.36 g, 1.15 mmol) in chloroform (10 ml) is treated at room temperature with N-bromosuccinimide (0.21 g, 1.2 mmol, 1.05 eq.). After stirring for 20 min, the mixture is partitioned between water (150 ml) and ethyl acetate (50 ml). The organic phase is washed with brine (100 ml), dried (magnesium sulfate) and filtered, and the solvent is removed by evaporation in vacuo to afford the title compound as an orange solid. The product is used in the next step without further purification.

Workup

  1. customthe mixture is partitioned between water (150 ml) and ethyl acetate (50 ml)
  2. washThe organic phase is washed with brine (100 ml)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation in vacuo

Sources & evidence

ORD record
ord-28bc31faf3b746c18256815d2d2dd775
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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