Sodium Hydroxide → Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

HRID 473125Notes

Reaction equation

HRID 473125 reaction equation
[F:1][C:2]([F:15])([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=1)[C:3]([O:5]CC)=[O:4].[OH-].[Na+:17]>CO.C1COCC1>[F:15][C:2]([F:1])([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]=1)[C:3]([O-:5])=[O:4].[Na+:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66609741Ethyl 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

Product 1

HCID 66609989Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetateYield 100.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To ethyl 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate (560 mg, 2.55 mmol) in 1:1 MeOH/THF (10 mL) at rt was added 1 M NaOH (2.8 mL, 2.8 mmol). The solution was stirred for 10 min and then concentrated to dryness to afford sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate (548 mg, quantitative). 1H NMR (300 MHz, DMSO-d6) δ 7.66 (dd, 1H), 7.79 (dt, 2H), 8.54 (d, 1H).

Workup

  1. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f9fb1c81fe9f4c2889e94c5ca79860a4
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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