Carbon tetrabromide → 1-benzyl-3-(bromomethyl)-5-phenyl-1H-pyrazole

HRID 1397458Notes

Reaction equation

HRID 1397458 reaction equation
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([N:32]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34](CO)=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:32]1[C:36]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:35][C:34]([CH2:1][Br:5])=[N:33]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67324379(1-benzyl-5-phenyl-1H-pyrazol-3-yl)methanol

Product 1

HCID 673248621-benzyl-3-(bromomethyl)-5-phenyl-1H-pyrazoleYield 43%

Procedure

Carbon tetrabromide (2.5 g, 7.6 mmol) and then triphenylphosphine (2.0 g, 7.6 mmol) was added to (1-benzyl-5-phenyl-1H-pyrazol-3-yl)methanol (1.0 g, 3.8 mmol) in dicholomethane (38 mL) at 0° C. Upon completion of the reaction as monitored by LCMS, the reaction was filtered through silica washing with methylene chloride and then purified on an ISCO using 0-30% ethyl acetate/hexanes to give 1-benzyl-3-(bromomethyl)-5-phenyl-1H-pyrazole (0.5 g, yield 43%). MS (ESI) m/z: Calculated for C17H15BrN2: 326.04. found: 327.0 (M+H)+.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe reaction was filtered through silica washing with methylene chloride
  3. custompurified on an ISCO

Sources & evidence

ORD record
ord-c9916c202c494304ad9ab686d9b7da83
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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