Cyclohexene → Chlorodicyclohexylborane

HRID 741531Notes

Reaction equation

HRID 741531 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[Cl:7][BH2:8].CSC>[Hg].C(OCC)C>[CH:1]1([B:8]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[Cl:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 178419200HCID 178419200, compound

Product 1

HCID 4413142ChlorodicyclohexylboraneYield 80%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL round bottom flask fitted with a rubber septum, a magnetic stirring bar, and a connecting tube attached to a mercury bubbler was cooled in an ice bath and charged with diethyl ether (90 mL) under inert atmosphere. Cyclohexene (21.2 mL, 210 mmol) was added, followed by the slow addition of monochloroborane-methyl sulfide (11.6 mL, 100 mmol). The mixture was stirred at 0° C. for 2 h. The solvent was removed under reduced pressure (25° C., 12 Torr). Distillation provided pure dicyclohexylchloroborane (δ 76 ppm in hexane), 16.85 g, 80% yield, bp 104°-105° C. (0.5 mm). Synthesis of this product by this process can readily be carried out on a molar scale.

Workup

  1. customA 250-mL round bottom flask fitted with a rubber septum, a magnetic stirring bar, and a connecting tube
  2. temperaturewas cooled in an ice bath
  3. customThe solvent was removed under reduced pressure (25° C., 12 Torr)
  4. distillationDistillation

Sources & evidence

ORD record
ord-46c142f5b92c4b87ac3ca017268b5a0f
Source dataset
uspto-grants-1996_09
Patent number
US05552081

Reaction notes

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