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

HRID 1582630Notes

Reaction equation

HRID 1582630 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9]O)=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]C(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][Br:30])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 219623285-(Bromomethyl)-2,3-dichloropyridineYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dichloro-5-(hydroxymethyl)pyridine (275 mg) was dissolved in dichloromethane (10 ml) and stirred in the presence of triphenylphosphine (444 mg) and tetrabromometliane (641 mg) overnight. The solution was concentrated in vacuo and the residue purified by column chromatography using isohexane: 2.5% ethyl acetate as eluent to yield the product as a white solid (270 mg, 73%). NMR: δ 4.75 (s, 2H), 8.25 (m, 1H), 8.5 (m, 1H); m/z 242 (M+H+).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-8111d67015b141f6958f9fa630553319
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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