Carbon tetrabromide → HCID 22645492, compound

HRID 2414388Notes

Reaction equation

HRID 2414388 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:6]=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22645497HCID 22645497, compound

Product 1

HCID 22645492HCID 22645492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of allyl 6-(hydroxymethyl)pyridine-2-carboxylate (1.0 g, 5.17 mmol) in 20 mL of CH2Cl2 is cooled to 0° C. under argon and 3.43 g (10.3 mmol) of CBr4 is added. Then, 1.5 g (5.69 mmol) of triphenyl phosphine is added in several portions over 20 min. The reaction is allowed to stir at 0° C. for 3 h and is then concentrated in vacuo and applied to a short silica gel column. Elution with 1:1 EtOAc-hexane yields allyl 6-(bromomethyl)pyridine-2-carboxylate as an oil.

Workup

  1. concentrationis then concentrated in vacuo
  2. washElution with 1:1 EtOAc-hexane

Sources & evidence

ORD record
ord-95be7dfe08494a29bf7a0b4d78bdefd3
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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