Phosphorus tribromide → HCID 44819211, compound

HRID 1496903Notes

Reaction equation

HRID 1496903 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]([F:22])([F:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[N:15]2)=[CH:10][CH:9]=1>CCOCC>[Br:2][CH2:19][C:16]1[CH:17]=[CH:18][N:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]([F:22])([F:21])[F:5])=[CH:9][CH:10]=2)[N:15]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 44819039HCID 44819039, compound

Product 1

HCID 44819211HCID 44819211, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

PBr3 (0.312 mL, 3.32 mmol) was added to a solution of alcohol 67 (0.858 g, 3.32 mmol) in ether (15 mL) at 0° C. The mixture was stirred at room temperature for 17 h, then cooled to 0° C., quenched with ice, and partitioned between CH2Cl2 and water. Column chromatography of the organic portion on silica gel (eluting with CH2Cl2) gave 3-(bromomethyl)-1-[4-(trifluoromethoxy)phenyl]-1H-pyrazole (68) (0.952 g, 89%) as a white solid: mp 71-73° C.; 1H NMR (CDCl3) δ 7.84 (d, J=2.5 Hz, 1H), 7.69 (d, J=9.1 Hz, 2H), 7.31 (d, J=9.1 Hz, 2H), 6.54 (d, J=2.5 Hz, 1H), 4.56 (s, 2H). APCI MS m/z 321, 323 [M+H]+.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with ice
  3. custompartitioned between CH2Cl2 and water

Sources & evidence

ORD record
ord-87b36775319946ab8734bbf2cd6641c7
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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