Trifluoroacetic acid → 5-Benzyl-4-bromo-1-methyl-1H-pyrazole

HRID 1778201Notes

Reaction equation

[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)O.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[CH2:8]([C:3]1[N:4]([CH3:7])[N:5]=[CH:6][C:2]=1[Br:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 14520172(4-bromo-1-methyl-1H-pyrazol-5-yl)(phenyl)methanol

Product 1

HCID 867185475-Benzyl-4-bromo-1-methyl-1H-pyrazole

Conditions

Temperature: 50 °C

Procedure

(4-Bromo-2-methyl-2H-pyrazol-3-yl)-phenyl-methanol (0.50 g; 1.87 mmol) is treated with 3.0 ml TFA and Triethylsilane (1.49 ml; 9.36 mmol) and is heated to 50° C. for 16 hours. The product is purified via reversed phase chromatography under acid conditions.

Workup

customThe product is purified via reversed phase chromatography under acid conditions

Sources & evidence

ORD record: ord-504c76ee750e4f9b862a2eb144fcba8c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266891B2

Reaction notes

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