Dichloromethane → HCID 178519520, compound

HRID 1862067Notes

Reaction equation

HRID 1862067 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11].[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].C(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>O>[Cl:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[O:16].[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7611Bis(eta-cyclopentadienyl) ironHCID 691102-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 178519520HCID 178519520, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A thoroughly dried, 2-L three-necked, round-bottomed flask was equipped with a mechanical stirrer, a funnel for the addition of air-sensitive solid, and a two-necked adapter holding a thermometer and a gas-inlet tube. The flask is charged with 74.4 g (0.4 mol) of ferrocene, 53.4 mL (0.4 mol) of 2-chlorobenzoyl chloride and 600 mL of CH2Cl2, and the addition funnel contains 56 g (0.42 mol) of AlCl3. The mixture was stirred in an ice bath and AlCl3 was added in small potions at such a rate that the reaction mixture remained below 5° C. This addition took about 20 min. and the mixture was stirred for 30 min. in the ice bath and was stirred for 2 h at rt. The reaction mixture was cooled in an ice bath and 400 ml of water was added. The mixture was loaded to a separatory funnel, the organic layer was separated, and aqueous layer was extracted with 400 mL of CH2Cl2. The combined CH2Cl2 solution are washed with 100 mL of water, 100 mL of 10% NaOH, 100 mL of brine and dried with Na2SO4. After filtration, the solution was evaporated to dryness at reduced pressure to give 129.2 g (>99%) of (2-chlorobenzoyl) ferrocene as a dark red solid.

Workup

  1. customA thoroughly dried
  2. custom2-L three-necked, round-bottomed flask was equipped with a mechanical stirrer, a funnel for the addition of air-sensitive solid, and a two-necked adapter
  3. customremained below 5° C
  4. additionThis addition
  5. stirringwas stirred for 2 h at rt
  6. temperatureThe reaction mixture was cooled in an ice bath
  7. customThe mixture was loaded to a separatory funnel
  8. customthe organic layer was separated
  9. extractionaqueous layer was extracted with 400 mL of CH2Cl2
  10. washThe combined CH2Cl2 solution are washed with 100 mL of water, 100 mL of 10% NaOH, 100 mL of brine
  11. dry with materialdried with Na2SO4
  12. filtrationAfter filtration
  13. customthe solution was evaporated to dryness at reduced pressure

Sources & evidence

ORD record
ord-2810f538bea1426a92733dfa7c8e8e89
Source dataset
uspto-grants-2003_03
Patent number
US06534657B2

Reaction notes

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