Hydrochloric Acid → 2-(5-Bromo-pyridin-2-yl)-5-chloro-pentanoic acid

HRID 220202Notes

Reaction equation

HRID 220202 reaction equation
C[O:2][C:3](=[O:16])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)[CH2:5][CH2:6][CH2:7][Cl:8].O[Li].O.Cl>C1COCC1.CO>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH:4]([CH2:5][CH2:6][CH2:7][Cl:8])[C:3]([OH:16])=[O:2])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 592382862-(5-Bromo-pyridin-2-yl)-5-chloro-pentanoic acid methyl ester

Product 1

HCID 592382662-(5-Bromo-pyridin-2-yl)-5-chloro-pentanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(5-Bromo-pyridin-2-yl)-5-chloro-pentanoic acid methyl ester (2.0 g, 6.5 mmol) in THF/MeOH (5/1) 30 mL, LiOH.H2O (1.092 g, 26 mmol.) was added. After the solution was stirred at room temperature for 16 h, the solution was neutralized with 2N HCl to pH 5-6. The mixture was evaporated to dryness under reduced pressure, then EtOAc (50 mL) was added. The organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to obtain of an oil product without further purification. MS: calc'd 291 (MH+), exp 291 (MH+).

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. additionEtOAc (50 mL) was added
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain of an oil product without further purification

Sources & evidence

ORD record
ord-4ebe2d6d93c74bae9923542d5cf1fbd1
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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