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Sodium → (5-Fluoro-2-phenoxy-phenyl)-(5-methoxy-2-[2-(tosyloxy-)-ethoxy]-benzyl}-amine

HRID 1717516
Notes
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Reaction equation

HRID 1717516 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.[CH3:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([O:26][CH2:27][CH2:28][O:29][S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[C:22]([CH:25]=1)[CH:23]=O.[Na]>ClC(Cl)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH:8][CH2:23][C:22]2[CH:25]=[C:18]([O:17][CH3:16])[CH:19]=[CH:20][C:21]=2[O:26][CH2:27][CH2:28][O:29][S:30]([C:33]2[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=2)(=[O:32])=[O:31])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 5360545SodiumHCID 196271325-Fluoro-2-phenoxyanilineHCID 59765853HCID 59765853, compound

Product 1

HCID 86621789(5-Fluoro-2-phenoxy-phenyl)-(5-methoxy-2-[2-(tosyloxy-)-ethoxy]-benzyl}-amineYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6365
1,1-Dichloroethane
Solvent

Procedure

To stirred solution of 9.1 g (45 mmol) 1b, 15.8 g (45 mmol) 5a and one drop of glacial acid in 60 ml dichloroethane (pH=5) were added 14.8 g (70 mmol) sodium tris-acetoxy hydro borane. The reaction mixture was stirred over night and diluted with 5 ml water. The pH value was adjusted with aqueous sodium hydroxyd solution to pH=8-9. The mixture was extracted three times with dichloromethane. The combined organic phases were washed with water and brine and were dried with magnesium sulfate. The desired crude product 5b was obtained in 71% yield (17.2 g, 32.0 mmol) as yellow oil. The crude product 5b was used without further purification.

Workup

  1. extractionThe mixture was extracted three times with dichloromethane
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialwere dried with magnesium sulfate

Sources & evidence

ORD record
ord-7be09e1615004a95bd8380c33dda484b
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803960B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes