Tetrahydrofuran → 2-Chloropyridine-5-boronic acid

HRID 402590Notes

Reaction equation

HRID 402590 reaction equation
O1CCCC1.Br[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[N:11][CH:12]=1.C[O:15][B:16](OC)[O:17]C>CCCCCC>[Cl:13][C:10]1[N:11]=[CH:12][C:7]([B:16]([OH:17])[OH:15])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 38450342-Chloropyridine-5-boronic acid

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
10 °C

Procedure

In a flask replaced by nitrogen, tetrahydrofuran solution (80 g) of 5-bromo-2-chloropyridine (9.6 g, 50.0 mmol) was charged, and cooled at 10° C., and then n-hexane solution of n-butyllthium (15% by weight, 24.6 g, 57.5 mmol) was added dropwise at 10° C. Next, at 10° C., trimethoxyborane (5.7 g, 55.0 mmol) was added dropwise. After 30 minutes from adding dropwise, cooling bath was removed off, and the reaction mixture was stirred at room temperature overnight. However, 6-chloro-3-pyridylboronic acid could not be obtained.

Workup

  1. additionwas charged
  2. additionAfter 30 minutes from adding dropwise
  3. temperaturecooling bath
  4. customwas removed off

Sources & evidence

ORD record
ord-7ea39feb39e341e39ab6c67b83bd1231
Source dataset
uspto-grants-2014_06
Patent number
US08742127B2

Reaction notes

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