Carbon tetrabromide → 2-(Bromomethyl)-5-(trifluoromethyl)pyridine

HRID 2075557Notes

Reaction equation

HRID 2075557 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9]O)=[N:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>ClCCl>[Br:33][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 3820787(5-(Trifluoromethyl)pyridin-2-yl)methanol

Product 1

HCID 214410942-(Bromomethyl)-5-(trifluoromethyl)pyridineYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-trifluoromethyl-pyridin-2-yl)-methanol (1.65 g) in dichloromethane (20 ml) at 0° C. (ice-bath) under nitrogen was added triphenylphosphine (3.66 g, 13.98 mmol) in portions, followed by addition of carbon tetrabromide (3.23 g) in portions. The ice-bath was removed and the flask was sealed with a glass stopper. The reaction mixture was gently stirred for 1 hour. The crude reaction mixture was loaded onto a silica gel column (120g), and eluted with methyl acetate/hexane to give 2-bromomethyl-5-trifluoromethyl-pyridine as a light orange oil (1.65 g, 73%).

Workup

  1. customThe ice-bath was removed
  2. customthe flask was sealed with a glass stopper
  3. customThe crude reaction mixture
  4. washeluted with methyl acetate/hexane

Sources & evidence

ORD record
ord-979d75ea5926416099c0b40ecefa369c
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

Loading…