Bromine → 5-Bromo-3-phenoxypyridin-2-amine

HRID 1809545Notes

Reaction equation

[O:1]([C:8]1[C:9]([NH2:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Br:15][C:12]1[CH:13]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([NH2:14])=[N:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 3 L flask was charged with 3-phenoxypyridin-2-amine (63.6 g, 342 mmol) and CHCl3 (1500 mL). The reaction was cooled to 0° C. and bromine (21.0 mL, 410 mmol) was added dropwise. The reaction was stirred for 1 hour. Another 1 mL of bromine was added and the reaction was poured into saturated aqueous NaHCO3 (1500 mL) and extracted with CH2Cl2. The organic layer was dried with sodium sulfate and 25 g charcoal. The mixture was filtered through Celite and concentrated in vacuo. The residue was dissolved in CH2Cl2 and passed through a plug of silica (1 L) eluting with 30% EtOAc/Hexanes to afford 5-bromo-3-phenoxypyridin-2-amine (64.02 g, 70.70% yield).

Workup

extractionextracted with CH2Cl2
dry with materialThe organic layer was dried with sodium sulfate and 25 g charcoal
filtrationThe mixture was filtered through Celite
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in CH2Cl2
washeluting with 30% EtOAc/Hexanes

Sources & evidence

ORD record: ord-20398c5ff18c4a0c847ae3f45da6d1d2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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