4-Bromophenol → HCID 59240368, compound

HRID 1672991Notes

Reaction equation

HRID 1672991 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11]Br)[N:8]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[N:7]=1)=[O:5])[CH3:2].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][O:28][C:25]2[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=2)[N:8]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 59239995HCID 59239995, compound

Product 1

HCID 59240368HCID 59240368, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 500 mL flask was weighed 19.3 g (53 mmol) of 5-bromomethyl-1-(2,6-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester, 13.7 g (79 mmol) of 4-bromophenol, 10.9 mg (79 mmol) of potassium carbonate, and 100 mL of ACN. The reaction mixture was heated to reflux for 4 h. After cooling, the crude reaction mixture 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 column chromatography on silica eluting with DCM-methanol (100:0 to 98:2) to afford 5-(4-bromophenoxymethyl)-1-(2,6-dichlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester as an off white solid (25.3 g, 100%); 1H NMR (400 MHz, CDCl3): δ 7.45 (m, 6H), 7.06 (s, 1H), 6.67 (d J=8.8 Hz 2H), 4.88 (s, 2H), 4.43 (q, J=7.07 Hz 2H), 1.41 (t, J=7.07 Hz 3H), MS (ES): 491 [M+Na]+.

Workup

  1. customInto a 500 mL flask was weighed
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 4 h
  4. temperatureAfter cooling
  5. customthe crude reaction mixture
  6. washwas washed into a separatory funnel with ethyl acetate and water
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography on silica eluting with DCM-methanol (100:0 to 98:2)

Sources & evidence

ORD record
ord-7679e4349d0e4b558bcc07eda5742cd6
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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