Hydrochloric Acid → (5-BroMo-6-chloropyridin-3-yl)Methanol

HRID 2234224Notes

Reaction equation

HRID 2234224 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.Cl>C1COCC1>[Cl:11][C:3]1[C:2]([Br:1])=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Product 1

HCID 20583217(5-BroMo-6-chloropyridin-3-yl)MethanolYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-6-chloronicotinic acid (3.0 g, 13 mmol) in THF (20 mL) at 25° C. was added borane (1.0 M in THF, 25 mL, 25 mmol) dropwise. The solution was stirred for 3 h, after which 1.0 M HCl was added dropwise to quench the reaction and the contents of the flask were transferred to a separatory separation funnel. The organic layer was separated and the aqueous phase further extracted with EtOAc (3×). The combined organic phases were dried over Na2SO4 and concentrated, to furnish 2-chloro-3-bromo-5-hydroxymethylpyridine as a white solid (1.0 g, 37%). GC-MS: Exact mass calcd for C6H6BrClNO [M+H]+, 223. Found 223.

Workup

  1. customto quench
  2. customthe reaction
  3. customthe contents of the flask were transferred to a separatory separation funnel
  4. customThe organic layer was separated
  5. extractionthe aqueous phase further extracted with EtOAc (3×)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d2a0df25196b4cc99526ee28d4bdd169
Source dataset
uspto-grants-2010_05
Patent number
US07709649B2

Reaction notes

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