Phenyltrimethylammonium bromide dibromide → HCID 86721221, compound

HRID 1750380Notes

Reaction equation

HRID 1750380 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[C:8]([C:18](=[O:20])[CH3:19])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[Br-:21].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C>C1COCC1>[Br:21][CH2:19][C:18]([C:8]1[CH:7]=[N:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:9]=1[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)=[O:20]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 86721220HCID 86721220, compound

Product 1

HCID 86721221HCID 86721221, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the compound (260 mg, 0.95 mmol) obtained in step 4 in THF (5 mL) was added dropwise a solution of trimethylphenylammonium tribromide (359 mg, 0.95 mmol) in THF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 14 hr, and the precipitate was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 2→45% ethyl acetate/hexane) to give 2-bromo-1-(1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl)ethanone (107 mg, 0.305 mmol, 31.9%) as a white powder.

Workup

  1. filtrationthe precipitate was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (solvent gradient; 2→45% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7941acbc3bc7455c858fbb2a9e8e98a6
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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