Carbon tetrabromide → 2-(Bromomethyl)-3-fluoropyridine

HRID 1486309Notes

Reaction equation

HRID 1486309 reaction equation
[F:1][C:2]1[C:3]([CH2:8]O)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]C(Br)(Br)Br>ClCCl>[Br:29][CH2:8][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19703803(3-Fluoropyridin-2-yl)methanol

Product 1

HCID 216131732-(Bromomethyl)-3-fluoropyridineYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 285 mg (2.242 mmol) of (3-fluoropyridin-2-yl)methanol (CAS: 31181-79-0) in dry dichloromethane (9 ml) in an ice-water bath and under an argon atmosphere was admixed with 882 mg (3.36 mmol) of triphenylphosphine and 1.12 g (3.36 mmol) of tetrabromomethane. The reaction mixture was stirred at room temperature for 22 hours. The solvent was evaporated off and the residue was purified by flash chromatography using a prepacked silica gel cartridge (mobile phase: cyclohexane-ethyl acetate, gradient 15% to 30%), which gave 156 mg (11% yield, 98% pure) of the target compound.

Workup

  1. customThe solvent was evaporated off
  2. customthe residue was purified by flash chromatography
  3. customgave 156 mg (11% yield, 98% pure) of the target compound

Sources & evidence

ORD record
ord-b06ad1c19c914f41ac70f024944e6878
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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