Carbon tetrabromide → HCID 57941503, compound
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]([F:49])([F:48])[C:22]1[C:26]([CH2:27]O)=[CH:25][N:24]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:23]=1.C(Br)(Br)(Br)[Br:51]>ClCCl>[Br:51][CH2:27][C:26]1[C:22]([C:21]([F:49])([F:48])[F:20])=[N:23][N:24]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Triphenylphosphine (0.54 g, 2.1 mmol) was added to a solution of (3-trifluoromethyl-1-trityl-1H-pyrazol-4-yl)-methanol (0.6 g, 1.5 mmol) in dichloromethane (25 mL). The resulting solution was cooled to −20° C. and a solution of carbon tetrabromide (0.54 g, 1.6 mmol) in dichloromethane (5 mL) was added in four portions. The solution was stirred for 5 min at −20° C. and then at for 3 h at 0° C. Further portions of triphenylphosphine (0.17 g, 0.65 mmol) and carbon tetrabromide (0.24 g, 0.72 mmol) were added. The solution was stirred for 3 h, and further portions of triphenylphosphine (0.54 g, 2 mmol) and carbon tetrabromide were added. The solution was stirred for 30 min and then the solvent was evaporated and the residue purified by flash chromatography, eluting with 5-10% ethyl acetate/petroleum ether to give 4-bromomethyl-3-trifluoromethyl-1-trityl-1H-pyrazole (0.30 g, 43%) as a white solid.
Workup
- customat for 3 h
- customat 0° C
- stirringThe solution was stirred for 3 h
- stirringThe solution was stirred for 30 min
- customthe solvent was evaporated
- customthe residue purified by flash chromatography
- washeluting with 5-10% ethyl acetate/petroleum ether
Sources & evidence
- ORD record
- ord-7b4528b8d0a3441bb0f56a03ac0798aa
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622492B2
Reaction notes
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