Hydrogen Bromide → HCID 86720214, compound

HRID 1753998Notes

Reaction equation

HRID 1753998 reaction equation
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5].[BrH:18].OO>>[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([Br:18])=[CH:13][C:3]=1[C:4]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:5]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 784Hydrogen PeroxideHCID 63447326HCID 63447326, compound

Product 1

HCID 86720214HCID 86720214, compoundYield 795.6%

Procedure

The above-described method (Example 1) was repeated to react hexyl 2-amino-3-methylbenzoate (2.50 g, 10 mmol) with hydrogen bromide (2.21 g, 13 1 mmol, 48% in water) and hydrogen peroxide (1.72 g, 15.0 mmol, 30% in water). Following working up similar to Example 1 and additional column chromatography, hexyl 2-amino-5-bromo-3-methylbenzoate (2.5 g, 78.8% of theory, >99 area % LC) was obtained as a brown oil.

Sources & evidence

ORD record
ord-cfe568c900fc4c06b5fccfabd4ef0ae1
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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