4-Bromophenol → HCID 19034153, compound

HRID 265911Notes

Reaction equation

HRID 265911 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]I)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Product 1

HCID 19034153HCID 19034153, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-4 (6.45 g, 19.0 mmol), 4-bromophenol (3.29 g, 19 mmol), and Cs2CO3 (3.10 g, 9.5 mmol) in 50 mL of DMF was stirred at room temperature for 18 hr. The solution was then diluted with 200 mL ethyl acetate and washed with H2O (4×100 mL), then dried over Na2SO4, filtered and concentrated. Flash chromatography (silica, 30% EtOAc/hexanes) gave 36-1 as a white solid.

Workup

  1. washwashed with H2O (4×100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3ed9629fbfb44485b5a96afdfa3e2a03
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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