Water → 2-(4-bromophenoxy)-5-(trifluoromethyl)pyridine

HRID 709512Notes

Reaction equation

HRID 709512 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 28220572-(4-bromophenoxy)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(4-Bromophenoxy)-5-(trifluoromethyl)pyridine (2) was prepared by heating a mixture of 4-bromophenol (1.0 eq, Aldrich), 2-chloro-5-(trifluoromethyl)pyridine (0.9 eq, Aldrich), and K2CO3 (2 eq) in 25 mL of CH3CN at 80° C. under argon for 14 hours. After cooling to room temperature, water (30 mL) was added, extracted with EtOAc (2×100 mL), concentrated and purified by column (silica gel, Hexanes, then Hexanes/EtOAc 10/1) to give compound 2: 1H-NMR (400 MHz, CDCl3) δ 8.45 (s, 1H), 7.94 (ddd, 1H, 0.6, 2.6 & 8.6 Hz), 7.56 (d, 2H, 8.9 Hz), 7.05-7.08 (m, 3H).

Workup

  1. custom2-(4-Bromophenoxy)-5-(trifluoromethyl)pyridine (2) was prepared
  2. temperatureby heating
  3. extractionextracted with EtOAc (2×100 mL)
  4. concentrationconcentrated
  5. custompurified by column (silica gel, Hexanes

Sources & evidence

ORD record
ord-c1d928ac8e804c7a8c0a0a2f326e6a33
Source dataset
uspto-grants-2015_11
Patent number
US09181185B2

Reaction notes

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