Tetrahydrofuran → 4-chloro-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 339945Notes

Reaction equation

HRID 339945 reaction equation
[CH3:1][N:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][CH:4]=[N:3]1.[Cl:16]N1C(=O)CCC1=O.O1CCCC1>>[Cl:16][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[B:7]1[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 31398ChlorosuccinimideHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 755256674-chloro-1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleYield 92.6%

Procedure

A solution of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.00 g, 4.81 mmol) and N-chlorosuccinimide (0.671 g, 5.05 mmol) in tetrahydrofuran (10 mL, 100 mmol) was stirred at 70° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by combi-flash chromatography and eluted with EtOAc/hexane (10-80%). The purification afforded 1.08 g (78% yield) of the desired product as white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by combi-flash chromatography
  3. washeluted with EtOAc/hexane (10-80%)
  4. customThe purification

Sources & evidence

ORD record
ord-6d52fc3be286486a94642d77c60f9a6d
Source dataset
uspto-grants-2014_11
Patent number
US08895571B2

Reaction notes

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