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2-Fluorophenol → Ethyl 2-(2-fluorophenoxy)propanoate

HRID 348315
Notes
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Reaction equation

HRID 348315 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[CH2:20]([O:19][C:17](=[O:18])[CH:16]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 10796Cesium carbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 57719284Ethyl 2-(2-fluorophenoxy)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Fluorophenol (0.30 mol), Cs2CO3 (197.0 g, 0.61 mol), and ethyl 2-bromopropionate (54.3 g, 0.30 mol) were combined in anhydrous DMF (1000 mL) and stirred at 90° C. under an atmosphere of nitrogen. After 16 h, the DMF was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL) and washed twice with water and once with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to produce an oil.

Workup

  1. customthe DMF was removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  3. washwashed twice with water and once with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto produce an oil

Sources & evidence

ORD record
ord-95e3049befcd40758a43eced547af7f9
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176224B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes