Potassium Carbonate → HCID 86670932, compound

HRID 515274Notes

Reaction equation

HRID 515274 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([OH:35])([C:31]([F:34])([F:33])[F:32])[C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]([OH:35])([C:27]([F:28])([F:29])[F:30])[C:31]([F:32])([F:33])[F:34])=[CH:24][CH:25]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-olHCID 623476394-(2-Bromo-4-nitrophenoxy)piperidine

Product 1

HCID 86670932HCID 86670932, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(2-Bromo-4-nitrophenoxy)piperidine (10.96 mmol, 3.3 g), 2-(4-(bromomethyl)-phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (10.96 mmol, 3.69 g) and potassium carbonate (32.9 mmol, 4.54 g) were combined in acetonitrile (40 mL) and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue dissolved in dichloromethane (150 mL). The organic phase was washed with water (2×50 mL) then brine (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane) to afford the title compound (5.25 g). MS (ESI) m/z 558.8 [M+H]+

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue dissolved in dichloromethane (150 mL)
  3. washThe organic phase was washed with water (2×50 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-8dd348dbd1c546cb9b81b9b05e74eccb
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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