Carbon tetrabromide → 2-(2-Bromoethyl)pyrazine

HRID 2192355Notes

Reaction equation

HRID 2192355 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1.C(Br)(Br)(Br)[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:11][CH2:2][CH2:3][C:4]1[CH:9]=[N:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5222472-(pyrazin-2-yl)ethanol

Product 1

HCID 583484082-(2-Bromoethyl)pyrazineYield 223.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2′-hydroxyethyl)pyrazine (0.91 g) in 30 mL dichloromethane at 0° C. was added carbon tetrabromide (2.65 g) followed by triphenylphosphine (2.1 g) portionwise. The solution became very dark. After stirring for 1 h the reaction mixture was adsorbed onto HMN diatomaceous earth and purified by silica gel chromatography eluting with 0-5% MeOH/dichloromethane to give a cream solid (3.07 g) that was purified further by silica gel chromatography eluting with 0-50% EtOAc/pentane to give the sub-titled compound (0.47 g, 34%) as a yellow oil.

Workup

  1. custompurified by silica gel chromatography
  2. washeluting with 0-5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-899c63a6320c4740873fe13180737df6
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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