2-Bromo-2-methylpropionyl bromide → HCID 86672885, compound

HRID 1752834Notes

Reaction equation

HRID 1752834 reaction equation
[Br:1][C:2]([CH3:7])([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][C:2]([CH3:7])([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 86672885HCID 86672885, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared in 87% yield (3.53 g, 11.3 mmol) from the reaction of 2-bromo-2-methylpropanoyl bromide (3.0 g, 13 mmol) with O-benzylhydroxylamine hydrochloride (2.13 g, 13 mmol) via general procedure A. Rf=0.58 (3:1, hexanes:EtOAc); mp=88.6-91.1° C.; 1H-NMR (500 MHz, CDCl3): δ 9.05 (br s, 1H), 7.45-7.34 (m, 5H), 4.94 (s, 2H), and 1.93 (s, 6H); 13C-NMR (126 MHz, CDCl3): δ 169.7, 134.9, 129.6, 129.1, 128.8, 78.4, 59.5, and 32.6; FT-IR (neat) 3195 (br), 3034, 2954, 2890, 1652 (s), 1505, 1469, 1454, 1112, 1032, 1004 cm-1. HRESI-MS: calcd □ for C11H18BrN2O2 (M+NH4)+ 289.0546, observed 289.0543.

Sources & evidence

ORD record
ord-51e909c531a4419f827ec7b01463e6d9
Source dataset
uspto-grants-2015_10
Patent number
US09163033B2

Reaction notes

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