4-Bromophenol → HCID 59240083, compound

HRID 1672996Notes

Reaction equation

HRID 1672996 reaction equation
Br[CH2:2][C:3]1[N:4]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:2][C:3]2[N:4]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 59240334HCID 59240334, compound

Product 1

HCID 59240083HCID 59240083, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 250 mL flask was weighed 570 mg (1.52 mmol) of 2-Bromomethyl-1-(2,6-dichlorophenyl)-4-trifluoromethyl-1H-imidazole, 394 mg (2.25 mmol) of 4-bromophenol, 310 mg (2.25 mmol) of potassium carbonate, and 20 mL of acetonitrile. The flask was heated in an oil bath to reflux for 4 h. The crude reaction was washed into a separatory funnel with ethyl acetate and water. The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel flash chromatography by column chromatography eluting with MeOH-DCM (0:100 to 2:98) to afford 2-(4-Bromophenoxymethyl)-1-(2,6-dichloro-phenyl)-4-trifluoromethyl-1H-imidazole as an off white solid (417 mg, 59%); 1H NMR (400 MHz, CDCl3): δ 7.96 (d J=8.6 Hz 2H), 7.68 (d J=8.3 Hz 2H), 7.46 (m, 5H), 7.32 (m, 1H), 6.88 (d J=8.84 Hz 2H), 5.10 (s, 2H), 3.08 (s, 3H), MS (ES): 465 [M+H]+.

Workup

  1. customInto a 250 mL flask was weighed
  2. temperatureThe flask was heated in an oil bath
  3. temperatureto reflux for 4 h
  4. customThe crude reaction
  5. washwas washed into a separatory funnel with ethyl acetate and water
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel flash chromatography by column chromatography
  11. washeluting with MeOH-DCM (0:100 to 2:98)

Sources & evidence

ORD record
ord-b874b89c304f447cac762b7226ea8ac4
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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