Methanol → HCID 86609793, compound

HRID 1175620Notes

Reaction equation

HRID 1175620 reaction equation
[Li+].[OH-:2].[Br:3][C:4]1[N:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[C:11]#N)=[CH:6][CH:5]=1.C[OH:16]>O>[Br:3][C:4]1[N:9]=[CH:8][C:7]([C:10]([CH3:14])([CH3:13])[C:11]([OH:16])=[O:2])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 23134433HCID 23134433, compound

Product 1

HCID 86609793HCID 86609793, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of LiOH (252 mg, 10.5 mmol) in MeOH (15 mL) and water (5 mL) was added 2-(6-bromopyridin-3-yl)-2-methylpropanenitrile (example 40c) (800 mg, 3.5 mmol) and the reaction mixture was heated at 85° C. for 48 hrs. The methanol was evaporated and aqueous NaOH (1N, 10 mL) was added and the solution was washed with EtOAc, acidified with aq. HCl (6N) to pH˜4-5 and extracted with EtOAc. The organic layer was suuccessively washed with water and brine, dried over MgSO4, filtered and evaporated to give 700 mg (96%) of 2-(6-Bromopyridin-3-yl)-2-methylpropanoic acid (MS+H, 243.8).

Workup

  1. customThe methanol was evaporated
  2. additionaqueous NaOH (1N, 10 mL) was added
  3. washthe solution was washed with EtOAc
  4. extractionextracted with EtOAc
  5. washThe organic layer was suuccessively washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-03109d2051d84df4a6b1d5d3afaff775
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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