Carbon tetrabromide → 3-Bromo-2-(bromomethyl)-6-chloro-4-methylpyridine

HRID 1508503Notes

Reaction equation

HRID 1508503 reaction equation
[Br:1][C:2]1[C:3]([CH2:10]O)=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8].C(Br)(Br)(Br)[Br:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:10][Br:13])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 77230709(3-Bromo-6-chloro-4-methylpyridin-2-yl)methanol

Product 1

HCID 772307103-Bromo-2-(bromomethyl)-6-chloro-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (3-bromo-6-chloro-4-methylpyridin-2-yl)methanol (22.9 g, 97 mmol) in CH2Cl2 (1.5 L) was cooled to 0° C. CBr4 (48.2 g, 145 mmol) was added, followed by Ph3P (38.1 g, 145 mmol). The reaction was stirred at 0° C. for 20 minutes and then warmed to r.t. for 16 hours. The reaction was then concentrated and the residue was purified by flash chromatography on silica gel with 0 to 10% EtOAc/heptanes to afford of 3-bromo-2-(bromomethyl)-6-chloro-4-methylpyridine. 1H NMR (CDCl3, 500 MHz) δ 7.16 (s, 1H), 4.67 (s, 2H), 2.43 (s, 3H).

Workup

  1. temperaturewarmed to r.t. for 16 hours
  2. concentrationThe reaction was then concentrated
  3. customthe residue was purified by flash chromatography on silica gel with 0 to 10% EtOAc/heptanes

Sources & evidence

ORD record
ord-d0063562fb8a4623bc54a0d7a851e10a
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

Loading…