Bis(triphenylphosphanium) dibromide → HCID 59240053, compound

HRID 1672987Notes

Reaction equation

HRID 1672987 reaction equation
[Br-:1].[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[N:48]1[C:52]([CH2:53]O)=[CH:51][C:50]([C:55]([F:58])([F:57])[F:56])=[N:49]1>>[Br:1][CH2:53][C:52]1[N:48]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[Cl:41])[N:49]=[C:50]([C:55]([F:58])([F:57])[F:56])[CH:51]=1

Participants

3

Reactant 2

HCID 22664940Bis(triphenylphosphanium) dibromideHCID 59240012HCID 59240012, compound

Product 1

HCID 59240053HCID 59240053, compound

Procedure

A dry 250 mL flask was charged with triphenylphosphonium dibromide (6.3 g, 14.9 mmol) and a solution of [2-(2-chlorophenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-methanol (3.54 g in 100 mL of CH2Cl2) was added portionwise. The reaction was stirred at room temperature for 2 h then was washed into a separatory funnel with water and CH2Cl2. The CH2Cl2 was separated, dried (MgSO4), and concentrated in vacuo. The crude bromide was purified by silica gel flash chromatography (Jones Flashmaster, 70 g Silica gel, gradient elution from 100% hexanes to 10% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo to afford 5-bromomethyl-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole as a colorless oil, yield: 2.74 g (64% for both steps); 1H NMR (400 MHz, CDCl3): δ 7.35-7.55 (m, 4H), 6.70 (s, 1H), 4.21 (br s, 2H).

Workup

  1. washthen was washed into a separatory funnel with water and CH2Cl2
  2. customThe CH2Cl2 was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude bromide was purified by silica gel flash chromatography (Jones Flashmaster, 70 g Silica gel, gradient elution from 100% hexanes to 10% ethyl acetate over 30 minutes)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f2383ea49224aa9b7e77e22222468a7
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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