Hydrogen Bromide → HCID 89964215, compound

HRID 1846238Notes

Reaction equation

HRID 1846238 reaction equation
[Br:1][C:2]1[C:7]([O:8]C)=[C:6]([F:10])[CH:5]=[CH:4][N:3]=1.FC1C=CN=C(N)C=1OC.Br.BrBr.N([O-])=O.[Na+].[OH-].[Na+]>>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([F:10])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 6

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 24408BromineHCID 23668193Sodium NitriteHCID 89964305HCID 89964305, compoundHCID 89964810HCID 89964810, compound

Product 1

HCID 89964215HCID 89964215, compound

Conditions

Temperature
0 °C

Procedure

2-bromo-4-fluoro-3-methoxypyridine. To a 0° C. solution of 4-fluoro-3-methoxypyridin-2-amine (1 eq.) and 48% HBr (10 eq.) is added bromine (3 eq.) dropwise, followed by the addition of 40% NaNO2 (5.5 eq.). The reaction is stirred at 0° C. until judged complete by TLC. The reaction mixture is adjusted to pH 13 with 50% NaOH (aq). The aqueous solution is extracted with EtOAc. The combined EtOAc layers are dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give the title compound.

Workup

  1. extractionThe aqueous solution is extracted with EtOAc
  2. dry with materialThe combined EtOAc layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-a9316fb4733145068ed887fc5a5f20e0
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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