Hydrochloric Acid → (5-Bromopyridin-2-yl)acetic acid

HRID 1753080Notes

Reaction equation

HRID 1753080 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1)C(OCC)=O)C.[Li+].[OH-].Cl>C1COCC1.O.CC(O)C.C(Cl)Cl>[Br:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:5][C:4]([OH:18])=[O:3])=[N:12][CH:13]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59238270Diethyl 2-(5-bromopyridin-2-yl)malonate

Product 1

HCID 46238459(5-Bromopyridin-2-yl)acetic acid

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl(5-bromopyridin-2-yl)malonate (Preparation 84, 5.28 g, 16.70 mmol) in THF (50 mL) was added a solution of LiOH (2.10 g, 50.13 mmol) in water (12.5 mL) and the reaction was heated to 60° C. for 3 hours. The reaction was cooled and acidified to pH 3-4 with 2N HCl and diluted with 20% IPA in DCM. The organic layer was collected, dried over sodium sulphate and concentrated in vacuo. The crude residue was triturated with hexane to afford the title compound.

Workup

  1. temperatureThe reaction was cooled
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was triturated with hexane

Sources & evidence

ORD record
ord-a7c254e7bbef4d899dca09697df36216
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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