2-Fluorobenzoyl chloride → HCID 19036987, compound

HRID 865386Notes

Reaction equation

HRID 865386 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Sn](Cl)(Cl)(Cl)Cl.[CH3:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:18]=1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:18]1[N:19]([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[C:20]2[C:25]([C:17]=1[CH3:16])=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:5]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 24287Tin tetrachlorideHCID 19036947HCID 19036947, compound

Product 1

HCID 19036987HCID 19036987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.91 ml of 2-fluorobenzoyl chloride in 50 ml of dry DCM was cooled in an ice/salt bath. To the solution was added 0.86 ml (1.9 It g) of tin (IV) chloride. The mixture was stirred at -5° to 0° C. for 10 minutes after which was added 2.0 g of 2-(3-methyl-1H-indol-1-yl)-1H-isoindole-1,3-(2H)dione. The reaction mixture was stirred at 0° C. for 1 hour, allowed to warm to room temperature, cooled again in an ice bath, poured onto ice, extracted twice with ethyl acetate, washed with water, brine, dried (Na2SO4), filtered and concentrated to a green-yellow solid (2.67 g). The solid was chromatographed on silica gel, eluting with 15% acetone/heptane to provide 1.99 g of a solid, which was recrystallized from ethanol, m.p. 197°-199° C.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  2. temperaturecooled again in an ice bath
  3. additionpoured onto ice
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a green-yellow solid (2.67 g)
  9. customThe solid was chromatographed on silica gel
  10. washeluting with 15% acetone/heptane

Sources & evidence

ORD record
ord-51d10476326449cfa6f8bdb219214848
Source dataset
uspto-grants-1996_10
Patent number
US05565579

Reaction notes

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