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Water → 2-(2,3-Difluorophenyl)-2-methylpropanoic acid

HRID 2078092
Notes
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Reaction equation

HRID 2078092 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([CH3:13])([CH3:12])[C:10]#N.[OH2:14].[OH:15]S(O)(=O)=O>O1CCOCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([CH3:13])([CH3:12])[C:10]([OH:15])=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 11976442HCID 11976442, compound

Product 1

HCID 639898282-(2,3-Difluorophenyl)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(2,3-difluorophenyl)-2-methylpropanenitrile (9.5 g, 52 mmol) in 50 mL dioxane was treated with 10 mL H2O and concentrated H2SO4 (3 mL, 105 mmol). The resulting mixture was stirred at 110° C. for 16 hours, M+1=201. The reaction was then cooled to room temperature. The mixture was extracted with EtOAc and the organic layer discarded. The water layer was acidified with concentrated HCl, extracted with EtOAc, washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give 4.74 g of the title compound as a pale yellow solid. MS (m/z)=201 (M+H)+.

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. extractionextracted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad0dff67d81d4ad9b123f982cc6eb89c
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928139B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes