Hydrogen Bromide → Methyl 3-bromopyrazine-2-carboxylate

HRID 1184916Notes

Reaction equation

HRID 1184916 reaction equation
N[C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[BrH:12].BrBr.N([O-])=O.[Na+]>O>[Br:12][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 72669Methyl 3-aminopyrazinecarboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 13318551Methyl 3-bromopyrazine-2-carboxylateYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-amino-2-pyrazinecarboxylate (13.06 mmol, 2 g) in hydrobromic acid (13.06 mmol, 7.4 ml, 1.057 g) at 0° C. was added bromine (38.9 mmol, 2 mL, 6.22 g) drop wise and then a solution of sodium nitrite (33.3 mmol, 2.3 g) in water (4 mL). The reaction was stirred for 2 h at 0° C. and the reaction mixture was extracted with CH2Cl2. Organic layer was dried and evaporated to give crude methyl 3-bromopyrazine-2-carboxylate 101 (1.2 gr, 43%). (m/z)=217 and 219 (M+H)+.

Workup

  1. extractionthe reaction mixture was extracted with CH2Cl2
  2. customOrganic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-4799b0d91e054ef183f66dbb1c7d0366
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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