Lithium Hydroxide → 2-(3-Bromophenyl)-2,2-difluoroacetic acid

HRID 2110758Notes

Reaction equation

HRID 2110758 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:17])[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)([F:9])[F:8])C>CO.O.O>[Br:16][C:12]1[CH:11]=[C:10]([C:7]([F:8])([F:9])[C:6]([OH:17])=[O:5])[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 53419381Ethyl 2-(3-bromophenyl)-2,2-difluoroacetate

Product 1

HCID 287403302-(3-Bromophenyl)-2,2-difluoroacetic acidYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide (0.13 g, 3.12 mmol) is added to a solution of (3-bromo-phenyl)-difluoro-acetic acid ethyl ester (0.29 g, 1.04 mmol) in methanol/water (8 mL, 3:1) and the reaction mixture is stirred overnight at room temperature. The mixture is diluted with water and volatiles are removed in vacuo. The aqueous is extracted once with diethyl ether, acidified to pH 2, and extracted twice with ethyl acetate. The combined extracts are dried over magnesium sulfate, filtered and concentrated in vacuo to afford (3-bromo-phenyl)-difluoro-acetic acid (250 mg), which is used in the next step without further purification. LCMS: RT=2.26 minutes; MS: 249, 251(M−H).

Workup

  1. customare removed in vacuo
  2. extractionThe aqueous is extracted once with diethyl ether
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4ccd2bdb20f4a96b6429f438d9512ab
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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