Hydrogen Bromide → 2-Bromo-5-iodo-3-nitropyridine

HRID 1434641

반응식

[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](N)=[N:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[BrH:18]>>[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Br:18])=[N:6][CH:7]=1

참가 물질

반응물 4

HCID 260Hydrogen Bromide

HCID 14923Ammonium Hydroxide

HCID 33844682-Amino-5-iodo-3-nitropyridine

HCID 23668193Sodium Nitrite

생성물 1

HCID 186197852-Bromo-5-iodo-3-nitropyridine수율 23%

실험 절차

5-iodo-3-nitro-2-aminopyridine (5.6 g, 21.1 mmol) and concentrated HBr (60 mL) were stirred at room temperature for ten minutes. Sodium nitrite (11.7 g, 170 mmol) was then slowly added followed by CuBr (3.9 g, 27.2 mmol). Stirring continued overnight. The mixture was poured into 1:1 NH4OH:H2O, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 9:1 hexane:ethyl acetate to yield 5-iodo-3-nitro-2-bromopyridine (1.618 g, 23%) as a colorless solid.

후처리

extractionH2O, extracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe crude residue was purified by flash chromatography

출처 및 근거

ORD 기록: ord-68c9d6171e4c4c63aa75cb8747ad4930
출처 데이터셋: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07615567B2

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