Pyrophosphoric acid → HCID 178520530, compound

HRID 1195463Notes

Reaction equation

HRID 1195463 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=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].P(OP(O)(O)=O)(O)(O)=O.C(OCCCC)CCC.[OH-].[Na+]>O>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)=[O:7].[CH-:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[Fe+2:18]

Participants

7

Reactant 5

HCID 1023Pyrophosphoric acidHCID 7611Bis(eta-cyclopentadienyl) ironHCID 8909Butyl etherHCID 14798Sodium HydroxideHCID 758094-Bromobutyric acid

Product 1

HCID 178520530HCID 178520530, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.68 g of 4-bromobutyric acid, 1.86 g of ferrocene, 20 g of pyrophosphoric acid, 20 g of polyphosphoric acid, and 20 ml of di n-butylether were added and stirred while heating at 50° to 60° C. for 3 hours, then poured into water, made to be basic with sodium hydroxide, extracted with methylene chloride, and dried. The unreacted-ferrocene was removed with column chromatography, to obtain 2.75 g of 3-bromopropylferrocenyl ketone presented by the formula (D), in a yield of 82.0%. The proton nuclear magnetic resonance (1H--NMR) spectrum of the product is shown in FIG. 4. The result showed that the resulting product was the desired product (3-bromopropylferrocenyl ketone). ##STR11##

Workup

  1. temperaturewhile heating at 50° to 60° C. for 3 hours
  2. extractionextracted with methylene chloride
  3. customdried
  4. customThe unreacted-ferrocene was removed with column chromatography

Sources & evidence

ORD record
ord-8c690e8881d14c39aeb12f0f8e770b4a
Source dataset
uspto-grants-1992_05
Patent number
US05110964

Reaction notes

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