Triphenylphosphine → 3-Bromo-5-(bromomethyl)-4-chloropyridine

HRID 712751Notes

Reaction equation

HRID 712751 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Br:30])[C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 117667554(5-Bromo-4-chloropyridin-3-yl)methanol

Product 1

HCID 1176674043-Bromo-5-(bromomethyl)-4-chloropyridineYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Bromo-4-chloro-pyridin-3-yl)-methanol (400 mg, 1.80 mmol) and triphenylphosphine (566 mg, 2.16 mmol) are dissolved in DCM (20 mL) and N-bromosuccinimide (384 mg, 2.16 mmol) is added. The mixture is stirred for 4 hrs at room temperature. Then the reaction mixture is purified by flash column chromatography directly (without work-up) to give 300 mg of 3-bromo-5-bromomethyl-4-chloro-pyridine.

Workup

  1. customThen the reaction mixture is purified by flash column chromatography directly (without work-up)

Sources & evidence

ORD record
ord-258e8df7d41d49aa933c5e7b0716d9b9
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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