4-Bromopyrazole → (4-bromophenyl)(1H-pyrazol-4-yl)methanone

HRID 1392993Notes

Reaction equation

HRID 1392993 reaction equation
Br[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[Br:7][C:8]1[CH:19]=[CH:18][C:11]([C:12](N(OC)C)=[O:13])=[CH:10][CH:9]=1.C([Li])(C)(C)C>C(OCC)(=O)C>[Br:7][C:8]1[CH:19]=[CH:18][C:11]([C:12]([C:2]2[CH:3]=[N:4][NH:5][CH:6]=2)=[O:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 163754-BromopyrazoleHCID 109992524-Bromo-N-methoxy-N-methylbenzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 69200129(4-bromophenyl)(1H-pyrazol-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 4-bromopyrazole and 4-bromo-N-methoxy-N-methylbenzamide following the general method of Method 1 using two equivalents of t-butyllithium as the base. The crude product was re-crystallized from ethyl acetate and petroleum ether affording 0.28 g (44% yield) of the title compound as colorless crystals: mp 213-215° C.; 1H NMR (300 MHz, CD3OD) δ 7.95 (br s, 2 H), 7.58 (m, 2 H), 7.51 (m, 2 H); 13C NMR (100.5 MHz, CD3OD) δ 190.3, 139.6, 138.8, 133.4, 132.1, 128.6, 123.1; MS (TSP) m/z 251, 253 (M+1).

Sources & evidence

ORD record
ord-fb18ffffc9fb4d1181c8bee679d4f919
Source dataset
uspto-grants-2008_03
Patent number
US07345050B2

Reaction notes

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