Carbon tetrabromide → 4-(Bromomethyl)-3,5-dichloropyridine

HRID 1162194Notes

Reaction equation

HRID 1162194 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(Cl)Cl>[Br:31][CH2:8][C:7]1[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=1[Cl:10]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 17855219(3,5-Dichloropyridin-4-yl)methanol

Product 1

HCID 222277664-(Bromomethyl)-3,5-dichloropyridineYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3,5-dichloro-pyridin-4-yl)-methanol (918 mg, 5.15 mmol) was dissolved in dry DCM (25 mL). Triphenylphosphine (2.70 g, 10.3 mmoles) was added, and the mixture was stirred at room temperature for 10 minutes. The solution was then cooled to 0° C., and CBr4 (5.12 g, 15.4 mmoles) was added. The mixture was stirred at room temperature for 30 minutes, then the solvent was evaporated, and the crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt 95/5) to yield 850 mg of the title compound.

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. customthe solvent was evaporated
  4. customthe crude was purified by flash chromatography (SiO2, petroleum ether/AcOEt 95/5)

Sources & evidence

ORD record
ord-c5130feab1d040cf853617c8df3c865b
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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