3-Chlorophenol → HCID 57467445, compound

HRID 1890787Notes

Reaction equation

HRID 1890787 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:16]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:16]1([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 10796Cesium carbonateHCID 97595Ethyl 1-bromocyclobutanecarboxylate

Product 1

HCID 57467445HCID 57467445, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 3-chlorophenol (7.5 g, 58.0 mmol) in N,N-dimethylformamide (125 mL) was added cesium carbonate (28.3 g, 87 mmol) followed by the addition of ethyl 1-bromocyclobutanecarboxylate (9.8 mL, 58.0 mmol). The reaction mixture was stirred at 55° C. overnight. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. Purification by column chromatography (silica, heptane/ethyl acetate, 7:1) afforded ethyl 1-(3-chlorophenoxy)cyclobutanecarboxylate. MS (ESI+) m/z 255 (M+H)+.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification by column chromatography (silica, heptane/ethyl acetate, 7:1)

Sources & evidence

ORD record
ord-d603a6af06f24f38ad20a95b553236d7
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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