Dichloromethane → Chlorobutyl ferrocene

HRID 1183848Notes

Reaction equation

HRID 1183848 reaction equation
FC(F)(F)C(O)=O.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18].[BH4-].[Na+].[Cl:21]CCl>>[Cl:21][CH2:13][CH2:14][CH2:15][CH2:16][C-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 7611Bis(eta-cyclopentadienyl) ironHCID 4311764Sodium borohydride

Product 1

HCID 15346559Chlorobutyl ferrocene

Procedure

A cold solution of freshly distilled trifluoroacetic acid (5 ml) was added to a solution of the ferrocene derivative, 1-Oxo-4-chlorobutylferrocene I, (5 g, 17.2 mmole) in dry dichloromethane (15 ml) at 0° C. Sodium borohydride (0.78 g) was added to the reaction mixture at 0° C. and the reaction mixture was stirred overnight at this temperature. After completion of the reaction as indicated from TLC, the reaction was quenched by adding water (50 ml) and the mixture was extracted with dichloromethane (2×25 ml).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction was quenched
  3. additionby adding water (50 ml)
  4. extractionthe mixture was extracted with dichloromethane (2×25 ml)

Sources & evidence

ORD record
ord-0e39a71419bc4a98ae9c36d74090bfde
Source dataset
uspto-grants-2014_03
Patent number
US08664417B2

Reaction notes

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