Lithium hydroxide, monohydrate → HCID 87131485, compound

HRID 2201515Notes

Reaction equation

HRID 2201515 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18]C)=[O:17])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[CH2:1]([O:8][C:9]1[C:10]([C:16]([OH:18])=[O:17])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59418684Methyl 3-(benzyloxy)-6-bromopicolinate

Product 1

HCID 87131485HCID 87131485, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of methyl 3-(benzyloxy)-6-bromopicolinate (2.0 g, 6.20 mmol) and LiOH.H2O (0.71 g, 18.60 mmol) in 1,4-dioxane/H2O (100 mL/20 mL) was stirred at 40° C. overnight. The mixture was filtered and the filtrate was acidified to pH=3 by aqueous HCl (2 M) and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated to afford the product of 3-(benzyloxy)-6-bromopicolinic acid (1.87 g, yield: 97.9%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 7.52˜7.54 (m, 1H), 7.39˜7.41 (m, 2H), 7.24˜7.34 (m, 4H), 5.24 (s, 2H). MS (M+H)+: 308/310.

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b277fe49eca4ee299be090b47b132dc
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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