Water → HCID 89544754, compound

HRID 2283390Notes

Reaction equation

HRID 2283390 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[C:6]([F:16])[C:5]([CH:17](Br)Br)=[CH:4][CH:3]=1.C([OH:23])(C)C.O>[N+]([O-])([O-])=O.[Ag+].ClCCl>[C:8]([C:7]1[C:6]([F:16])=[C:5]([CH:4]=[CH:3][C:2]=1[Cl:1])[CH:17]=[O:23])(=[O:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3776IsopropanolHCID 89544515HCID 89544515, compound

Product 1

HCID 89544754HCID 89544754, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6344DichloromethaneSolvent

Procedure

Step 4 A mixture of (6-chloro-3-dibromomethyl-2-fluoro-phenyl)-phenyl-methanone (582 mg, 1.38 mmol), silver nitrate (469 mg, 2.76 mmol), isopropanol (10 ml) and water (2 ml) was stirred at room temperature overnight. Dichloromethane was added and the mixture was filtered under suction washing with isopropanol. The organic liquors were concentrated then purified by silica chromatography eluting with 0-20% ethyl acetate/petroleum ether furnishing 3-benzoyl-4-chloro-2-fluoro-benzaldehyde (222 mg oil, 90% clean). Analytical data as above

Workup

  1. filtrationthe mixture was filtered under suction
  2. washwashing with isopropanol
  3. concentrationThe organic liquors were concentrated
  4. customthen purified by silica chromatography
  5. washeluting with 0-20% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7fa7af75ac5d4723aaa094068a7416e3
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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