Ethanol → 5-Bromo-2-(tetrahydropyran-4-yl)nitrobenzene

HRID 74182

Reaction equation

HRID 74182 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.N[CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 4192234-AminotetrahydropyranHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 674988265-Bromo-2-(tetrahydropyran-4-yl)nitrobenzeneYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An eggplant flask was charged with 5-bromo-2-fluoronitrobenzene (3.0 g, 13.6 mmol), triethylamine (1.66 g, 16.3 mmol), 4-aminotetrahydropyran (1.52 g, 15.0 mmol), and ethanol (60 mL), and this was heated to reflux with stirring for 2 hours. After concentration of the reaction mixture under reduced pressure, water (60 mL) was added and this was stirred as is at room temperature for 30 minutes. The precipitated crystals were filtered off and washed with water. The crystals obtained were dried at reduced pressure with heating to yield the title compound (3.55 g, 86% yield) as a reddish-orange solid.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. stirringthis was stirred
  4. waitas is at room temperature for 30 minutes
  5. filtrationThe precipitated crystals were filtered off
  6. washwashed with water
  7. customThe crystals obtained
  8. customwere dried at reduced pressure
  9. temperaturewith heating

Sources & evidence

ORD record
ord-3a8229f9c17741f3846e907f5ce44fc5
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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