Hydrogen Bromide → HCID 54593425, compound

HRID 1754000Notes

Reaction equation

[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[BrH:14].OO>>[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:10]([Br:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Reactant 3

HCID 260Hydrogen Bromide

HCID 784Hydrogen Peroxide

HCID 19064948Ethyl 2-amino-3-methylbenzoate

Product 1

HCID 54593425HCID 54593425, compoundYield 89.1%

Procedure

The above-described method (Example 1) was repeated to react 2-ethyl 2-amino-3-methylbenzoate (16.29 g, 90.0 mmol) with hydrogen bromide (15.93 g, 94.5 mmol, 48% in water) and hydrogen peroxide (11.25 g, 99.0 mmol, 30% in water) and, following working up similar to Example 1, ethyl 2-amino-5-bromo-3-methylbenzoate (20.7 g, 89.1% of theory, >99 area % LC) was obtained as a brown oil.

Sources & evidence

ORD record: ord-3c7148b6f6d940b6ac570963aa3c6da3
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169198B2

Reaction notes

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