Water → HCID 58913633, compound

HRID 1296931Notes

Reaction equation

HRID 1296931 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[OH:20])[O:16][C:15]([CH3:21])=[C:14]([C:22]1[CH:27]=[CH:26][C:25](OC)=[CH:24][CH:23]=1)[C:13]2=[O:30].O.CCCCCC>CN(C=O)C>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[C:18]([Cl:1])[C:19]=1[OH:20])[O:16][C:15]([CH3:21])=[C:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:13]2=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 31398ChlorosuccinimideHCID 11197888HCID 11197888, compound

Product 1

HCID 58913633HCID 58913633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (0.27 g, 2 mmol) was added to a solution of 6-chloro-7-hydroxy-3-(4-methoxy-phenyl)-2-methyl-chromen-4-one (0.29 g, 1 mmol) in DMF (4 ml) and the solution stirred for 3 hrs. and at 50° C. for ˜3 hrs. The resulting solution was poured into water (50 ml) and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with water (5×50 ml) and saturated aqueous sodium chloride solution (30 ml). The solution was dried over anhydrous magnesium sulphate and concentrated to give a dark yellow oil. Trituration with hexane gave 6,8-dichloro-7-hydroxy-2-methyl-3-phenyl-chromen-4-one as a pale orange powder, dried in vacuo, (0.19 g)

Workup

  1. waitand at 50° C. for ˜3 hrs
  2. extractionextracted with ethyl acetate (2×30 ml)
  3. washThe combined extracts were washed with water (5×50 ml) and saturated aqueous sodium chloride solution (30 ml)
  4. dry with materialThe solution was dried over anhydrous magnesium sulphate
  5. concentrationconcentrated
  6. customto give a dark yellow oil

Sources & evidence

ORD record
ord-2af023d70d2645b5bb88558949593d1e
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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