Ethyl Acetate → Hydrogen Bromide

HRID 515157

Reaction equation

HRID 515157 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10].[Br:11]Br.C(OCC)(=O)C>CO.C(O)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([O:2][CH3:1])[CH:8]=1.[BrH:11]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 4592492-Methoxy-6-methylaniline

Product 2

HCID 260Hydrogen BromideHCID 106802184-bromo-2-methoxy-6-methylaniline

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

To solution of (2-methoxy-6-methyl-phenyl)-amine (14.5 g, 0.11 mol) in methanol (45.6 ml) and acetic acid (14.5 ml) is added dropwise a solution of bromine (5.45 ml) in acetic acid (45.6 ml) via an addition funnel at 0° C. The reaction mixture is allowed to warm to RT and stirred for 2 h at RT. Ethyl acetate (90 ml) is added and the solid is collected by filtration. The solid thus obtained is washed with ethyl acetate to obtain (4-bromo-2-methoxy-6-methyl-phenyl)-amine as hydrobromide.

Workup

  1. filtrationthe solid is collected by filtration
  2. customThe solid thus obtained
  3. washis washed with ethyl acetate

Sources & evidence

ORD record
ord-46bd0a0e1cb643b996597ccf74878b38
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Linked notes

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