Carbon tetrabromide → 5-(Bromomethyl)-2,3-dichloropyridine

HRID 1821475Notes

Reaction equation

HRID 1821475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[N:6][C:7]=1[Cl:8].C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][Br:12])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 219623285-(Bromomethyl)-2,3-dichloropyridineYield 130%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5,6-dichloro-3-pyridinemethanol (1.0 eq.) was taken up in dichloromethane and stirred overnight with carbon tetrabromide (1.5 eq.) and 1,3-bis(diphenylphosphino)propane (0.75 eq.) Ether was added to the solution and filtration followed by concentration of the filtrate afforded the 5,6-dichloro-3-bromomethylpyridine in 130% yield.

Workup

  1. additionwas added to the solution and filtration

Sources & evidence

ORD record
ord-dfe8add5cedf41f5b9d00e28731f9807
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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