Bromoform → 3-Bromo-6-(5-bromo-2-fluorophenyl)-1,2,4-triazine

HRID 2276769Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]2[N:13]=[N:12][C:11](N)=[N:10][CH:9]=2)[CH:7]=1.N(OCCC(C)C)=O.C(Br)(Br)[Br:25]>>[Br:25][C:11]1[N:12]=[N:13][C:8]([C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[F:15])=[CH:9][N:10]=1

Participants

Reactant 3

HCID 5558Bromoform

HCID 8053Isoamyl Nitrite

HCID 674534646-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amine

Product 1

HCID 866868233-Bromo-6-(5-bromo-2-fluorophenyl)-1,2,4-triazine

Conditions

Temperature: 80 °C

Procedure

6-(5-Bromo-2-fluorophenyl)-1,2,4-triazin-3-amine (4.5 g, 16.7 mmol) was dissolved in 25 mL of bromoform and heated to 80° C. Isoamyl nitrite (9.8 g, 83.5 mmol) was then added and stirred at 85° C. for 1 h. The reaction mixture was then concentrated and silica gel chromatography afforded a yellow solid (4.4 g), m/z=331.1 [M+H].

Workup

concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record: ord-4d0f94077c584075ae50dec8676e6204
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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