Pinacol → 2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2188321Notes

Reaction equation

HRID 2188321 reaction equation
[B:1]([Cl:4])(Cl)Cl.[OH:5][C:6]([C:9]([OH:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>CCCCC>[Cl:4][B:1]1[O:12][C:9]([CH3:11])([CH3:10])[C:6]([CH3:8])([CH3:7])[O:5]1

Participants

4

Reactant 2

HCID 6425PinacolHCID 25135Boron Trichloride

Product 1

HCID 139254112-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
20 °C

Procedure

About 82 mL of BCl3 is added dropwise over 30 minutes to a stirred solution of dry pinacol in pentane (1.3 L) at −30° C. The reaction mixture is stirred at 20° C. for 1 hour. A solid byproduct, B2[(OCMe2)2]3 is removed by filtration. The remaining solution is distilled to give about 90 grams of 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Workup

  1. customA solid byproduct, B2[(OCMe2)2]3 is removed by filtration
  2. distillationThe remaining solution is distilled

Sources & evidence

ORD record
ord-874ed6547d4e40258d25add6bd7084e2
Source dataset
uspto-grants-2002_06
Patent number
US06410764B1

Reaction notes

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