Cyclohexene → Chlorodicyclohexylborane

HRID 1769435Notes

Reaction equation

HRID 1769435 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 (δ76 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-1c9200db70a94595b30b9c79e9ef7b5b
Source dataset
uspto-grants-1995_01
Patent number
US05380940

Reaction notes

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