Hydrogen Bromide → HCID 86720215, compound

HRID 1753999Notes

Reaction equation

HRID 1753999 reaction equation
[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[BrH:20].OO>>[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][C:3]=1[C:4]([O:6][CH2:7][CH:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:5]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 55193855HCID 55193855, compound

Product 1

HCID 86720215HCID 86720215, compoundYield 98.6%

Procedure

The above-described method (Example 1) was repeated to react 2-ethylhexyl 2-amino-3-methylbenzoate (3.00 g, 10.6 mmol) with hydrogen bromide (2.33 g, 13 8 mmol, 48% in water) and hydrogen peroxide (1.81 g, 15.9 mmol, 30% in water). Following working up similar to Example 1 and additional column chromatography, 2-ethylhexyl 2-amino-5-bromo-3-methylbenzoate (2.7 g, 74.0% of theory, >99 area % LC) was obtained as a brown oil.

Sources & evidence

ORD record
ord-227c7c6ed1d7481393a6142a50221636
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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