2-Bromo-2-methylpropionyl bromide → HCID 86672883, compound

HRID 1752830Notes

Reaction equation

HRID 1752830 reaction equation
[Br:1][C:2](C)([CH3:6])[C:3](Br)=[O:4].Cl.[CH2:9]([O:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCOC(C)=O>[Br:1][CH:2]([CH3:6])[C:3]([NH:17][O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]

Participants

4

Reactant 2

HCID 886852-Bromo-2-methylpropionyl bromideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 86672883HCID 86672883, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 53% yield (631 mg, 2.44 mmol) from the reaction of 2-bromo-2-methylpropanoyl bromide (1.0 g, 4.6 mmol) with O-benzylhydroxylamine hydrochloride (742 mg, 4.6 mmol) via general procedure A. Rf=0.28 (3:1, hexanes:EtOAc); mp=75.3-77.4° C.; 1H-NMR (500 MHz, CDCl3): δ 9.61 (br s, 1H), 7.44-7.26 (m, 5H), 4.90 (s, 2H), 4.31 (q, J=7.7 Hz, 1H), and 1.77 (d, J=6.4 Hz, 3H); 13C-NMR (126 MHz, CDCl3): δ 167.5, 134.8, 129.45, 128.9, 128.7, 78.3, 40.5, and 22.2; FT-IR (neat) 3110 (br), 2924, 2852, 1675 (s), 1508, 1495, 1453, 1364, 1188, 1038, 1023 cm-1;

Sources & evidence

ORD record
ord-fabd5f7254a144f9b39f47ffe91f579a
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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